Phthalamide derivative, agricultural or horticultural insecticide, and method of use thereof

ABSTRACT

The present invention relates to a phthalamide derivative represented by the general formula (I):  
                 
 
wherein R 1 , R 2 , R 3 , X, Y, m, and n are as defined in the disclosure, which can be used as the active ingredient in an agricultural or horticultural insecticide that exhibits an excellent insecticidal effect even when used in a small active-ingredient amount.

TECHNICAL FIELD

The present invention relates to an agrohorticultural insecticidecontaining a phthalamide derivative as an active ingredient, and amethod of use thereof.

1. Background Art

Phthalamide derivatives similar to the present invention are known to beuseful as an agrohorticultural insecticide (see, for example, JapanesePatent Application Laid-Open (KOKAI) Nos. 11-240857, 2001-131141,2001-158764, 2001-240580, and 2001-335563). However, a phthalamidederivative having a particular substituent represented by the generalformula (I) has not been disclosed or suggested.

In crop production such as agriculture and horticulture, there stillexist large damages caused by insect pests or the like. Due to reasonssuch as appearance of insect pests resistant to existing insecticides, anovel agrohorticultural insecticide is desired to be developed.Moreover, as farmers are aged, various laborsaving application methodsare desired, and an agrohorticultural insecticide having a featuresuitable for such application methods is desired to be created.

2. Disclosure of the Invention

The present inventors strenuously studied in order to develop a novelagrohorticultural insecticide, and then have accomplished the presentinvention by finding that a phthalamide derivative represehted by thegeneral formula (I) is a novel compound described in documents; shows anexcellent insecticidal effect at a smaller dosage than those ofcompounds described in prior documents; and in particular, by soiltreatment, shows an elevated absorption translodation action from rootsand-thereby has an excellent insecticidal effect.

That is, the present invention relates to a phthalamide derivativerepresented by the general formula (I):

wherein R¹ represents hydrogen; C₃₋₆ cycloalkyl; halo C₃₋₆ cycloalkyl;phenyl; substituted phenyl having one or more substituents, which may bethe same or different, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; heterocyclyl; substitutedheterocyclyl having one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; or -A-(G)r in which A represents C₁₋₈ alkylene, C₃₋₆alkenylene, or C₃₋₆ alkynylene; G's may be the same or different andeach represents hydrogen; halogen; cyano; nitro; halo C₁₋₆ alkyl; C₃₋₆cycloalkyl; halo C₃₋₆ cycloalkyl; same or different di C₁₋₆alkoxyphosphoryl; same or different di C₁₋₆ alkoxythiophosphoryl;diphenylphosphino; diphenylphosphono; same or different C₁₋₆dialkylsulfonium; phenyl; substituted phenyl having one or moresubstituents, which may be the same or different, and selected fromhalogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;heterocyclyl; substituted heterocyclyl having one or more substituents,which may be the same or different, and selected from halogen, C₁₋₆alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio,halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; —Z—R⁴ in which Z represents—O—; —N(R⁵)— (R⁵ represents hydrogen; C₁₋₆ alkylcarbonyl; halo C₁₋₆alkylcarbonyl; C₁₋₆ alkoxycarbonyl; phenylcarbonyl; substitutedphenylcarbonyl having one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; C₁₋₆ alkylsulfonyl; or halo C₁₋₆ alkylsulfonyl); R⁴represents hydrogen; C₁₋₆ alkyl; halo C₁₋₆ alkyl; C₃₋₆ alkenyl; haloC₃₋₆ alkenyl; C₃₋₆ alkynyl; halo C₃₋₆ alkynyl; C₃₋₆ cycloalkyl; haloC₃₋₆ cycloalkyl; C₁₋₆ alkoxy C₁₋₆ alkyl; C₁₋₆ alkylthio C₁₋₆ alkyl;formyl; C₁₋₆ alkylcarbonyl; halo C₁₋₆ alkylcarbonyl; C₁₋₆alkoxycarbonyl; mono C₁₋₆ alkylaminocarbonyl; same or different di C₁₋₆alkylaminocarbonyl; mono C₁₋₆ alkylaminothiocarbonyl; same or differentdi C₁₋₆ alkylaminothiocarbonyl; same or different di C₁₋₆alkoxyphosphoryl; same or different di C₁₋₆ alkoxythiophosphoryl;phenyl; substituted phenyl having one or more substituents, which may bethe same or different, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; phenyl C₁₋₄ alkyl;substituted phenyl C₁₋₄ alkyl having on a ring one or more substituents,which may be the same or different, and selected from halogen, C₁₋₆alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio,halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; heterocyclyl; or substitutedheterocyclyl having one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; or —W—R⁶ in which W represents —S—, —SO—, —SO²—, —C(═O)—,—C(═S)—, or —C(═NOR⁷)— (R⁷ represents hydrogen; C₁₋₆ alkyl; halo C₁₋₆alkyl; C₃₋₆ alkenyl; halo C₃₋₆ alkenyl; C₃₋₆ alkynyl; C₃₋₆ cycloalkyl;phenyl C₁₋₄ alkyl; or substituted phenyl C₁₋₄ alkyl having on a ring oneor more substituents, which may be the same or different, and selectedfrom halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, haloC₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl); R⁶represents hydrogen; C₁₋₆ alkyl; halo C₁₋₆ alkyl; C₃₋₆ alkenyl; haloC₃₋₆ alkenyl; C₃₋₆ alkynyl; halo C₃₋₆ alkynyl; C₃₋₆ cycloalkyl; haloC₃₋₆ cycloalkyl; C₁₋₆ alkoxy C₁₋₆ alkyl; C₁₋₆ alkylthio C₁₋₆ alkyl; C₁₋₆alkoxy; halo C₁₋₆ alkoxy; C₁₋₆ alkylthio; halo C₁₋₆ alkylthio; amino;mono C₁₋₆ alkylamino; same or different di C₁₋₆ alkylamino; C₁₋₆ alkoxyC₁₋₆ alkylamino; C₁₋₆ alkylthio C₁₋₆ alkylamino; phenyl; substitutedphenyl having one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; phenyl C₁₋₄ alkyl; substituted phenyl C₁₋₄ alkyl havingon a ring one or more substituents, which may be the same or different,and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy,halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; phenylamino; substituted phenylamino having on a ring oneor more substituents, which may be the same or different, and selectedfrom halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, haloC₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;phenyl C₁₋₄ alkylamino; substituted phenyl C₁₋₄ alkylamino having on aring one or more substituents, which may be the same or different, andselected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, haloC₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl,halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;heterocyclyl; substituted heterocyclyl having one or more substituents,which may be the same or different, and selected from halogen, C₁₋₆alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio,halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; heterocyclic amino; orsubstituted heterocyclic amino having on a ring one or moresubstituents, which may be the same or different, and selected fromhalogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; rrepresents an integer of 1 to 3; and R⁴ or R⁶ together with A may form a4- to 8-membered ring that may be interrupted with 1 or 2 oxygen,sulfur, or nitrogen, which may be the same or different;

R² and R³ may be the same or different and each represents hydrogen,C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₃₋₆ alkenyl, halo C₃₋₆ alkenyl, C₃₋₆alkynyl, halo C₃₋₆ alkynyl, C₃₋₆ cycloalkyl, halo C₃₋₆ cycloalkyl, C₁₋₆alkoxy C₁₋₆ alkyl, C₁₋₆ alkylthio C₁₋₆ alkyl, formyl, C₁₋₆alkylcarbonyl, halo C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, mono C₁₋₆alkylaminocarbonyl, or same or different di C₁₋₆ alkylaminocarbonyl; andR² together with A, R¹, G, R⁴, or R⁶ may form a 4- to 8-membered ringthat may be interrupted with 1 or 2 oxygen, sulfur, or nitrogen, whichmay be the same or different;

X's may be the same or different and each represents halogen, nitro,amino, mono C₁₋₆ alkylamino, same or different di C₁₋₆ alkylamino, C₁₋₆alkylcarbonylamino, halo C₁₋₆ alkylcarbonylamino, C₁₋₆alkylsulfonylamino, halo C₁₋₆ alkylsulfonylamino, cyano, C₁₋₆ alkyl,halo C₁₋₆ alkyl, C₂₋₆ alkenyl, halo C₂₋₆ alkenyl, C₂₋₆ alkynyl, haloC₂₋₆ alkynyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylcarbonyloxy, haloC₁₋₆ alkylcarbonyloxy, C₁₋₆ alkylsulfonyloxy, halo C₁₋₆alkylsulfonyloxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; and two X's adjacent to each other on an aromatic ringmay together form a fused ring, and the fused ring may have one or moresubstituents, which may be the same or different, and selected fromhalogen, cyano, nitro, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, haloC₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl,halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;

m represents an integer of 0 to 2;

Y's may be the same or different and each represents halogen; nitro;cyano; C₁₋₆ alkyl; halo C₁₋₆ alkyl; cyclo C₃₋₆ alkyl; C₁₋₆ alkoxy; haloC₁₋₆ alkoxy; mono C₁₋₆ alkylamino; same or different di C₁₋₆ alkylamino;C₁₋₆ alkylthio; halo C₁₋₆ alkylthio; C₁₋₆ alkylsulfinyl; halo C₁₋₆alkylsulfinyl; C₁₋₆ alkylsulfonyl; halo C₁₋₆ alkylsulfonyl; phenyl;substituted phenyl having one or more substituents, which may be thesame or different, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; phenyl C₁₋₄ alkyl;substituted phenyl C₁₋₄ alkyl having on a ring one or more substituents,which may be the same or different, and selected from halogen, C₁₋₆alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio,halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; phenoxy; substituted phenoxyhaving one or more substituents, which may be the same or different, andselected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, haloC₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl,halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;phenylthio; substituted phenylthio having one or more substituents,which may be the same or different, and selected from halogen, C₁₋₆alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio,halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; heterocyclyl; or substitutedheterocyclyl having one or more substituents, which may be the same ordifferent, and selected from halogen, cyano, nitro, C₁₋₆ alkyl, haloC₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; and two Y's adjacent to eachother on an aromatic ring may together form a fused ring, and the fusedring may have one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; and Y together with R³ may form a 5- to 7-membered ringthat may be interrupted with 1 or 2 oxygen, sulfur, or nitrogen, whichmay be the same or different;

n represents an integer of 0 to 3,

and an agrohorticultural insecticide containing the compound as anactive ingredient, as well as a method of use thereof.

The compound of the present invention shows an excellent insecticidaleffect at a small dosage, and in particular, by soil treatment, shows anelevated absorption translocation action from roots.

BEST MODE FOR CARRYING OUT THE INVENTION

In the definition of the general formula (I) of a phthalamide derivativeof the present invention, “halogen” refers to chlorine, bromine, iodine,or fluorine; “C₁₋₆ alkyl” refers to a straight-chained or branched alkylgroup having 1 to 6 carbon atoms such as methyl, ethyl, normal propyl,isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl,normal pentyl, neopentyl, and normal hexyl; “halo C₁₋₆ alkyl” refers toa straight-chained or branched alkyl group having 1 to 6 carbon atomssubstituted by same or different, one or more halogens, for example,trifluoromethyl, difluoromethyl, perfluoroethyl, perfluoroisopropyl,chloromethyl, bromomethyl, 1-bromoethyl, and 2,3-dibromopropyl can bementioned; “C₁₋₈ alkylene” refers to a straight-chained or branchedalkylene group having 1 to 8 carbon atoms such as methylene, ethylene,propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene,dimethylethylene, and octamethylene; “C₃₋₆ alkenylene” or “C₃₋₆alkynylene” also refers to a straight-chained or branched alkenylenegroup or alkynylene group having 3 to 6 carbon atoms; “C₃₋₆ cycloalkyl”refers to an alicyclic alkyl group having 3 to 6 carbon atoms such ascyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

“Heterocyclyl” refers to a 5- or 6-membered heterocyclyl group havingone or more hetero atoms selected from oxygen, sulfur, or nitrogen, andthe examples include pyridyl, pyridine N-oxide, pyrimidinyl, furyl,tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl,tetrahydrothiopyranyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl,isothiazolyl, thiadiazolyl, imidazolyl, triazolyl, and pyrazolyl;examples of “fused ring” may include naphthalene, tetrahydronaphthalene,indene, indane, quinoline, quinazoline, indole, indoline, chromane,isochromane, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran,benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole,benzimidazole, and indazole.

The phthalamide derivative represented by the general formula (I) of thepresent invention sometimes contains one or more asymmetric carbon atomsor asymmetric centers in the structure, and also sometimes has two ormore optical isomers and diastereomers. The present invention intends toinclude all of each isomer and mixtures in which such isomers arecontained in any ratio. Also, the phthalamide derivative represented bythe general formula (I) of the present invention sometimes contains twogeometric isomers derived from a carbon-carbon double bond or acarbon-nitrogen double bond. The present invention also intends toinclude all of each geometric isomer and mixtures in which such isomersare contained in any ratio.

Among the phthalamide derivatives represented by the general formula (I)of the present invention, examples of preferable compounds may include aphthalamide derivative in which R¹ represents C₁₋₆ alkyl, C₁₋₆ alkylthioC₁₋₆ alkyl, C₁₋₆ alkylsulfinyl C₁₋₆ alkyl, or C₁₋₆ alkylsulfony C₁₋₆alkyl; R² and R³ represent hydrogen; X represents halogen; m represents1; Y represents halogen or C₁₋₆ alkyl; n represents an integer of 0 to2.

The phthalamide derivative represented by the general formula (I) of thepresent invention can be produced by, for example, the scheme shownbelow from an aniline derivative represented by the general formula (II)that can be produced by the schemes disclosed in UK Patent No. 2276379,WO94/21606, or the like, but also can be produced by the schemesdisclosed in Japanese Patent Laid-Open Nos. 11-240857 and 2001-131141.

wherein each of R¹, R², R³, X, Y, m, and n has the same meaning asdescribed above; and “halo” represents halogen.

The phthalamide derivative represented by the general formula (I-1) canbe produced by reacting the aniline derivative represented by thegeneral formula (II) with the phthalisoimide derivative represented bythe general formula (III-1) that can be produced by the scheme disclosedin Japanese Patent Laid-Open Nos. 11-240857 and 2001-131141 or the likein the presence or absence of an acid or base in an inert solvent.

The phthalamide derivative represented by the general formula (I-2) canbe produced by producing the phthalisoimide derivative representedbythegeneral formula (III-2) fromthe aniline derivative represented by thegeneral formula (II) by the scheme disclosed in Japanese PatentLaid-Open Nos. 11-240857 and 2001-131141 or the like, and then reactingthe phthalisoimide derivative with the amines represented by the generalformula (IV) in the presence or absence of an acid or base in an inertsolvent.

The phthalamide derivative represented by the general formula (I) can beproduced by reacting the phthalamide derivative represented by thegeneral formula (I-1) or (I-2) with the halides represented by thegeneral formula (V-1) or (V-2) in the presence of a non-hydrogen halideagent and an inert solvent.

In the definition of R¹ of the general formula (I), when R¹ represents-A-(G)r, and G represents —W—R⁶, the compound in which W represents —SO—or —SO₂— can be produced by subjecting the compound in which Wrepresents —S— to an oxidative reaction, for example, using an oxidizingagent such as m-chloroperbenzoic acid and hydrogen peroxide in anordinary manner.

1-1. General Formula (II)→General Formula (I-1) or General Formula(III-2)→General Formula (I-2)

This reaction can produce the intended product in accordance with themethod described in J. Med. Chem., 10, 982 (1967). This reaction can becarried out, if required, in the presence of a catalytic amount to anexcess amount of an acid or base.

Examples of acids that can be used in this reaction include organicacids such as acetic acid and trifluoroacetic acid, and inorganic acidssuch as hydrochloric acid and sulfuric acid. The use amount may beproperly selected in the range of from a catalytic amount to an excessmole with respect to the phthalisoimide derivative represented by thegeneral formula (III-1) or (III-2). Examples of bases include organicbases such as triethylamine and pyridine; and inorganic bases such aspotassium carbonate, sodium hydrogen carbonate, sodium carbonate, andsodium hydroxide. The use amount may be properly selected in the rangeof from a catalytic amount to an excess mole with respect to thephthalisoimide derivative represented by the general formula (III-1) or(III-2).

The reaction temperature can be from 0° C. to the boiling point of theinert solvent to be used. The reaction time is not constant depending onthe reaction scale, the reaction temperature, or the like, but withinthe range of several minutes to 48 hours. After completing the reaction,the intended product may be isolated from a reaction system containingthe intended product in an ordinary manner, and if required,purification by recrystallization, column chromatography, or the likecan be performed to produce the intended product.

1-2. General Formula (I-1)→General Formula (I) or (I-2)→General Formula(I)

Any inert solvent can be used in this reaction, as long as it does notmarkedly inhibit the progress of this reaction. The examples includearomatic hydrocarbons such as benzene, toluene, and xylene; halogenatedaromatic hydrocarbons such as fluorobenzene, chlorobenzene, anddichlorobenzene; halogenated hydrocarbons such as methylene chloride,chloroform, and carbon tetrachloride; chained or cyclic ethers such asdiethylether, dioxane, and tetrahydrofuran; esters such as ethylacetate; amides such as dimethylformamide and dimethylacetamide; acidssuch as acetic acid; and inert solvents such as dimethylsulfoxide and1,3-dimethyl-2-imidazolidinone. These inert solvents may be used aloneor as a mixture thereof.

Examples of non-hydrogen halide agents include organic bases such astriethylamine and pyridine; and inorganic bases such as potassiumcarbonate, sodium hydrogen carbonate, sodium carbonate, and sodiumhydroxide. This reaction is an equimolar reaction, and therefore anequimolar amount of each reaction agent may be used, but any of reactionagents can be used in excess.

The reaction temperature can be from room temperature to the refluxtemperature of the inert solvent to be used. The reaction time is notconstant depending on the reaction scale, the reaction temperature, orthe like, but may be properly selected in the range of several minutesto 48 hours.

After completing the reaction, the intended product may be isolated froma reaction system containing the intended product in an ordinary manner,and if required, purification by recrystallization, columnchromatography, or the like can be performed to produce the intendedproduct.

Typical compounds of phthalamides represented by the general formula (I)are shown in Tables 1 to 3 below, but the present invention is notlimited thereto.

In the tables, “n-” refers to normal, “s-” refers to secondary, “t-”refers to tertiary, “c-” refers to cyclo, “Ph” refers to phenyl, “Pyr”refers to pyridyl, and “C(*)” refers to asymmetric carbon. TABLE 1General formula (I-3) (I-3)

(R² = R³ = H) No. R1 Xm Yn Melting point (° C.) 1-1  CH₃ 3-I 2-CH₃ 1-2 C₂H₅ 3-I 2-CH₃ 1-3  n-C₃H₇ 3-I 2-CH₃ 1-4  i-C₃H₇ 3-I 2-CH₃ 1-5  c-C₃H₅3-I 2-CH₃ 1-6  n-C₄H₉ 3-I 2-CH₃ 1-7  s-C₄H₉ 3-I 2-CH₃ 1-8  t-C₄H₉ 3-I2-CH₃ 1-9  i-C₄H₉ 3-I 2-CH₃ 1-10  n-C₅H₁₁ 3-I 2-CH₃ 1-11  s-C₅H₁₁ 3-I2-CH₃ 1-12  t-C₅H₁₁ 3-I 2-CH₃ 1-13  c-C₅H₉ 3-I 2-CH₃ 1-14  CH₂CH═CH₂ 3-I2-CH₃ 1-15  CH₂C≡CH 3-I 2-CH₃ 1-16  CH(CH₃)CH═CH₂ 3-I 2-CH₃ 1-17 C(CH₃)₂CH═CH₂ 3-I 2-CH₃ 1-18  CH(CH₃)CH═CH-Ph 3-I 2-CH₃ 1-19 C(CH₃)₂CH═CH-2-Pyr 3-I 2-CH₃ 1-20  CH(CH₃)C≡CH 3-I 2-CH₃ 1-21 C(CH₃)₂C≡CH 3-I 2-CH₃ 1-22  C(CH₃)₂C≡Ph 3-I 2-CH₃ 1-23  C(CH₃)₂C≡C-2-Pyr3-I 2-CH₃ 1-24  C(CH₃)₂C≡CH 3-I 2-CH₃ 1-25  CH(CH₃)CF₃ 3-I 2-CH₃ 1-26 CH(CH₃)CH₂CF₃ 3-I 2-CH₃ 1-27  CH(CH₃)CH₂CH₂F 3-I 2-CH₃ 1-28 CH(CH₃)CH₂CH₂Cl 3-I 2-CH₃ 1-29  C(CH₃)₂CH₂CH₂F 3-I 2-CH₃ 1-30 C(CH₃)₂CH₂CH₂Cl 3-I 2-CH₃ 1-31  CH₂Ph 3-I 2-CH₃ 1-32  CH(CH₃)Ph 3-I2-CH₃ 1-33  C(CH₃)₂Ph 3-I 2-CH₃ 1-34  CH(CH₃)CH₂Ph 3-I 2-CH₃ 1-35 C(CH₃)₂CH₂Ph 3-I 2-CH₃ 1-36  CH(CH₃)-2-Pyr 3-I 2-CH₃ 1-37  CH(CH₃)-3-Pyr3-I 2-CH₃ 1-38  C(CH₃)₂-2-Pyr 3-I 2-CH₃ 1-39  C(CH₃)₂-3-Pyr 3-I 2-CH₃1-40  Ph 3-I 2-CH₃ 1-41  (3-SCH₃)Ph 3-I 2-CH₃ 1-42  (4-SCH₃)Ph 3-I 2-CH₃1-43  (3-CH₂SCH₃)Ph 3-I 2-CH₃ 1-44  (4-CH₂SCH₃)Ph 3-I 2-CH₃ 1-45 (3-SO₂NH₂)Ph 3-I 2-CH₃ 1-46  (4-SO₂NH₂)Ph 3-I 2-CH₃ 1-47  (3-CONH₂)Ph3-I 2-CH₃ 1-48  (4-CONH₂)Ph 3-I 2-CH₃ 1-49  3-Pyr 3-I 2-CH₃ 1-50 3-(4-SCH₃)Pyr 3-I 2-CH₃ 1-51  3-(2-CH₃-4-SCH₃)Pyr 3-I 2-CH₃ 1-52  i-C₃H₇3-I 2-Cl 1-53  s-C₄H₉ 3-I 2-Cl 1-54  t-C₄H₉ 3-I 2-Cl 1-55  s-C₅H₁₁ 3-I2-Cl 1-56  t-C₅H₁₁ 3-I 2-Cl 1-57  CH₂CO₂CH₃ 3-I 2-CH₃ 1-58 CH(CH₃)CO₂CH₃ 3-I 2-CH₃ 1-59  CH(CH₃)CO₂C₂H₅ 3-I 2-CH₃ 1-60 C(CH₃)₂CO₂CH₃ 3-I 2-CH₃ 1-61  C(CH₃)₂CO₂C₂H₅ 3-I 2-CH₃ 1-62 CH(CH₃)CH₂CO₂CH₃ 3-I 2-CH₃ 1-63  CH(CH₃)CH₂CO₂C₂H₅ 3-I 2-CH₃ 1-64 C(CH₃)₂CH₂CO₂CH₃ 3-I 2-CH₃ 1-65  C(CH₃)₂CH₂CO₂C₂H₅ 3-I 2-CH₃ 1-66 CH(CH₃)(CH₂)₂CO₂CH₃ 3-I 2-CH₃ 1-67  CH(CH₃)(CH₂)₂CO₂C₂H₅ 3-I 2-CH₃ 1-68 C(CH₃)₂(CH₂)₂CO₂CH₃ 3-I 2-CH₃ 1-69  C(CH₃)₂(CH₂)₂CO₂C₂H₅ 3-I 2-CH₃ 1-70 CH(CH₃)CH═CHCO₂CH₃ 3-I 2-CH₃ 1-71  CH(CH₃)CH═CHCO₂C₂H₅ 3-I 2-CH₃ 1-72 C(CH₃)₂CH═CHCO₂CH₃ 3-I 2-CH₃ 1-73  C(CH₃)₂CH═CHCO₂C₂H₅ 3-I 2-CH₃ 1-74 CH(CH₃)C≡CCO₂CH₃ 3-I 2-CH₃ 1-75  CH(CH₃)C≡CCO₂C₂H₅ 3-I 2-CH₃ 1-76 C(CH₃)₂C≡CCO₂CH₃ 3-I 2-CH₃ 1-77  C(CH₃)₂C≡CCO₂C₂H₅ 3-I 2-CH₃ 1-78  CH₂CN3-I 2-CH₃ 1-79  CH(CH₃)CN 3-I 2-CH₃ 1-80  C(CH₃)₂CN 3-I 2-CH₃ 1-81 CH(CH₃)CH₂CN 3-I 2-CH₃ 1-82  C(CH₃)₂CH₂CN 3-I 2-CH₃ 1-83  CH(CH₃)CONH₂3-I 2-CH₃ 1-84  C(CH₃)₂CONH₂ 3-I 2-CH₃ 1-85  CH(CH₃)CONHC₂H₅ 3-I 2-CH₃1-86  C(CH₃)₂CONHC₂H₅ 3-I 2-CH₃ 1-87  CH(CH₃)CON(C₂H₅)₂ 3-I 2-CH₃ 1-88 C(CH₃)₂CON(C₂H₅)₂ 3-I 2-CH₃ 1-89  CH(CH₃)CH₂CONHC₂H₅ 3-I 2-CH₃ 1-90 C(CH₃)₂CH₂CONHC₂H₅ 3-I 2-CH₃ 1-91  CH(CH₃)CH₂CON(C₂H₅)₂ 3-I 2-CH₃ 1-92 C(CH₃)₂CH₂CON(C₂H₅)₂ 3-I 2-CH₃ 1-93  C(CH₃)₂(CH₂)₂CONHC₂H₅ 3-I 2-CH₃1-94  C(CH₃)₂(CH₂)₂CON(C₂H₅)₂ 3-I 2-CH₃ 1-95  CH(CH₃)CH═CHCONHC₂H₅ 3-I2-CH₃ 1-96  CH(CH₃)CH═CHCON(C₂H₅)₂ 3-I 2-CH₃ 1-97  C(CH₃)₂CH═CHCONHC₂H₅3-I 2-CH₃ 1-98  C(CH₃)₂CH═CHCON(C₂H₅)₂ 3-I 2-CH₃ 1-99 CH(CH₃)C≡CCONHC₂H₅ 3-I 2-CH₃ 1-100 CH(CH₃)C≡CCON(C₂H₅)₂ 3-I 2-CH₃ 1-101C(CH₃)₂C≡CCONHC₂H₅ 3-I 2-CH₃ 1-102 C(CH₃)₂C≡CCON(C₂H₅)₂ 3-I 2-CH₃ 1-103CH(CH₃)CH═C 3-I 2-CH₃ 1-104 C(CH₃)₂CH═C 3-I 2-CH₃ 1-105 CH(CH₃)C(═O)CH₃3-I 2-CH₃ 1-106 C(CH₃)₂C(═O)CH₃ 3-I 2-CH₃ 1-107 CH(CH₃)CH═NOH 3-I 2-CH₃1-108 C(CH₃)₂CH═NOH 3-I 2-CH₃ 1-109 CH(CH₃)C(═O)CH₃ 3-I 2-CH₃ 1-110O(CH₃)₂C(═O)CH₃ 3-I 2-CH₃ 1-111 CH(CH₃)CH═NOCH₃ 3-I 2-CH₃ 1-112C(CH₃)₂CH═NOCH₃ 3-I 2-CH₃ 1-113 CH(CH₃)CH═NOC₂H₅ 3-I 2-CH₃ 1-114C(CH₃)₂CH═NOC₂H₅ 3-I 2-CH₃ 1-115 CH(CH₃)CH₂CH═NOCH₃ 3-I 2-CH₃ 1-116C(CH₃)₂CH₂CH═NOCH₃ 3-I 2-CH₃ 1-117 CH(CH₃)CH₂CH═NOC₂H₅ 3-I 2-CH₃ 1-118C(CH₃)₂CH₂CH═NOC₂H₅ 3-I 2-CH₃ 1-119 CH(CH₃)CH₂CH═NOCH₂Ph 3-I 2-CH₃ 1-120C(CH₃)₂CH₂CH═NOCH₂Ph 3-I 2-CH₃ 1-121 CH(CH₃)CH═NOCH₂CH═CH₂ 3-I 2-CH₃1-122 C(CH₃)₂CH═NOCH₂CH═CH₂ 3-I 2-CH₃ 1-123 CH(CH₃)CH═NOCH₂C≡CH 3-I2-CH₃ 1-124 C(CH₃)₂CH═NOCH₂C≡CH 3-I 2-CH₃ 1-125 CH(CH₃)CH═NO(CH₂)₂OCH₃3-I 2-CH₃ 1-126 C(CH₃)₂CH═NO(CH₂)₂OCH₃ 3-I 2-CH₃ 1-127CH(CH₃)₂CH═NO(CH₂)₂OC₂H₅ 3-I 2-CH₃ 1-128 C(CH₃)₂CH═NO(CH₂)₂OC₂H_(5 3-I)2-CH₃ 1-129 CH(CH₃)CH═NO(CH₂)₂SCH₃ 3-I 2-CH₃ 1-130C(CH₃)₂CH═NO(CH₂)₂SCH₃ 3-I 2-CH₃ 1-131 CH(CH₃)CH═NOCH₂CO₂C₂H₅ 3-I 2-CH₃1-132 C(CH₃)₂CH═NOCH₂CO₂C₂H₅ 3-I 2-CH₃ 1-133 CH(CH₃)C(CH₃)═NOCH₃ 3-I2-CH₃ 1-134 C(CH₃)₂C(CH₃)═NOCH₃ 3-I 2-CH₃ 1-135 CH(CH₃)C(CH₃)═NOC₂H₅ 3-I2-CH₃ 1-136 C(CH₃)₂C(CH₃)═NOC₂H₅ 3-I 2-CH₃ 1-137 C(CH₃)₂CH₂CO₂C₂H₅ 3-I2-Cl 1-138 C(CH₃)₂(CH₂)₂CO₂C₂H₅ 3-I 2-Cl 1-139 CH(CH₃)CH═CHCO₂C₂H₅ 3-I2-Cl 1-140 C(CH₃)₂CH═CHCO₂C₂H₅ 3-I 2-Cl 1-141 C(CH₃)₂C≡CCO₂C₂H₅ 3-I 2-Cl1-142 C(CH₃)₂CH₂CN 3-I 2-Cl 1-143 C(CH₃)₂CONHC₂H₅ 3-I 2-Cl 1-144C(CH₃)₂CON(C₂H₅)₂ 3-I 2-Cl 1-145 C(CH₃)₂CH₂CONHC₂H₅ 3-I 2-Cl 1-146C(CH₃)₂CH₂CON(C₂H₅)₂ 3-I 2-Cl 1-147 C(CH₃)₂(CH₂)₂CONHC₂H₅ 3-I 2-Cl 1-148C(CH₃)₂(CH₂)₂CON(C₂H₅)₂ 3-I 2-Cl 1-149 C(CH₃)₂CH═CHCONHC₂H₅ 3-I 2-Cl1-150 C(CH₃)₂CH═CHCON(C₂H₅)₂ 3-I 2-Cl 1-151 C(CH₃)₂CH═NOH 3-I 2-Cl 1-152C(CH₃)₂CH═NOCH₃ 3-I 2-Cl 1-153 C(CH₃)₂CH═NOCH₂CH═CH₂ 3-I 2-Cl 1-154C(CH₃)₂CH═NOCH₂C≡CH 3-I 2-Cl 1-155 C(CH₃)₂CH₂CH═NOH 3-I 2-Cl 1-156C(CH₃)₂CH₂CH═NOCH₃ 3-I 2-Cl 1-157 (CH₂)₂OCH₃ 3-I 2-CH₃ 1-158 (CH₂)₃OCH₃3-I 2-CH₃ 1-159 (CH₂)₂OC₂H₅ 3-I 2-CH₃ 1-160 CH(CH₃)CH₂OH 3-I 2-CH₃ 1-161C(CH₃)₂CH₂OH 3-I 2-CH₃ 1-162 CH(CH₃)CH₂OCH₃ 3-I 2-CH₃ 1-163C(CH₃)₂CH₂OCH₃ 3-I 2-CH₃ 1-164 CH(CH₃)CH₂OC₂H₅ 3-I 2-CH₃ 1-165C(CH₃)₂CH₂OC₂H₅ 3-I 2-CH₃ 1-166 CH(CH₃)CH₂OCH₂CH═CH₂ 3-I 2-CH₃ 1-167C(CH₃)₂CH₂OCH₂CH═CH₂ 3-I 2-CH₃ 1-168 CH(CH₃)CH₂OCH₂C≡CH 3-I 2-CH₃ 1-169C(CH₃)₂CH₂OCH₂C≡CH 3-I 2-CH₃ 1-170 CH(CH₃)(CH₂)₂OCH₃ 3-I 2-CH₃ 1-171C(CH₃)₂(CH₂)₂OCH₃ 3-I 2-CH₃ 1-172 CH(CH₃)(CH₂)₃OCH₃ 3-I 2-CH₃ 1-173C(CH₃)₂(CH₂)₃OCH₃ 3-I 2-CH₃ 1-174 CH(CH₃)(CH₂)₄OCH₃ 3-I 2-CH₃ 1-175C(CH₃)₂(CH₂)₄OCH₃ 3-I 2-CH₃ 1-176 CH(CH₃)CH₂OCH₂CF₃ 3-I 2-CH₃ 1-177C(CH₃)₂CH₂OCH₂CF₃ 3-I 2-CH₃ 1-178 CH(CH₃)CH₂OCH₂CN 3-I 2-CH₃ 1-179C(CH₃)₂CH₂OCH₂CN 3-I 2-CH₃ 1-180 CH(CH₃)CH₂OCH₂CO₂N(CH₃)₂ 3-I 2-Cl 1-181C(CH₃)₂CH₂OCH₂CO₂N(CH₃)₂ 3-I 2-Cl 1-182 CH(CH₃)CH₂O(CH₂)₂OCH₃ 3-I 2-CH₃1-183 C(CH₃)₂CH₂O(CH₂)₂OCH₃ 3-I 2-CH₃ 1-184 CH(CH₃)CH₂OCH₂Ph 3-I 2-CH₃1-185 C(CH₃)₂CH₂OCH₂Ph 3-I 2-CH₃ 1-186 CH(CH₃)CH₂O-Ph 3-I 2-CH₃ 1-187C(CH₃)₂CH₂O-Ph 3-I 2-CH₃ 1-188 CH(CH₃)CH₂O-2-Pyr 3-I 2-CH₃ 1-189C(CH₃)₂CH₂O-2-Pyr 3-I 2-CH₃ 1-190 CH(CH₃)₂CH₂O-3-Pyr 3-I 2-CH₃ 1-191C(CH₃)₂CH₂O-3-Pyr 3-I 2-CH₃ 1-192 CH(CH₃)CH₂OC(═O)CH₃ 3-I 2-CH₃ 1-193C(CH₃)₂CH₂OC(═O)CH₃ 3-I 2-CH₃ 1-194 CH(CH₃)CH₂OC(═O)CF₃ 3-I 2-CH₃ 1-195C(CH₃)₂CH₂OC(═O)CF₃ 3-I 2-CH₃ 1-196 CH(CH₃)CH₂OCO₂CH₃ 3-I 2-CH₃ 1-197C(CH₃)₂CH₂OCO₂CH₃ 3-I 2-CH₃ 1-198 CH(CH₃)CH₂OC(═O)NHCH₃ 3-I 2-CH₃ 1-199C(CH₃)₂CH₂OC(═O)NHCH₃ 3-I 2-CH₃ 1-200 CH(CH₃)CH₂OC(═O)NH(C₂H₅) 3-I 2-CH₃1-201 C(CH₃)₂CH₂OC(═O)NH(C₂H₅) 3-I 2-CH₃ 1-202CH(CH₃)CH₂OC(═O)N(CH₃)_(2 3-I) 2-CH₃ 1-203 C(CH₃)₂CH₂OC(═O)N(CH₃)₂ 3-I2-CH₃ 1-204 CH(CH₃)CH₂OC(═O)N(C₂H₅)₂ 3-I 2-CH₃ 1-205C(CH₃)₂CH₂OC(═O)N(C₂H₅)₂ 3-I 2-CH₃ 1-206 CH(CH₃)CH₂OC(═O)NHCH₂Ph 3-I2-CH₃ 1-207 C(CH₃)₂CH₂OC(═O)NHCH₂Ph 3-I 2-CH₃ 1-208C(CH₃)₂CH₂OCONH(CH₂)₃SCH₃ 3-I 2-CH₃ 1-209 C(CH₃)₂CH₂OCONH(CH₂)₂OCH₃ 3-I2-CH₃ 1-210 CH(CH₃)CH₂OC(═S)NHCH₃ 3-I 2-CH₃ 1-211 C(CH₃)CH₂OC(═S)NHCH₃3-I 2-CH₃ 1-212 CH(CH₃)CH₂OC(═S)N(C₂H₅)₂ 3-I 2-CH₃ 1-213C(CH₃)CH₂OC(═S)N(C₂H₅)₂ 3-I 2-CH₃ 1-214 CH(CH₃)CH₂OCONH(C₂H₅) 3-I 2-CH₃1-215 CH(CH₃)CH₂OCON(CH₃)₂ 3-I 2-CH₃ 1-216 CH(CH₃)CH₂OCON(C₂H₅)₂ 3-I2-CH₃ 1-217 CH(CH₃)CH₂OP(═O)(OCH₃)₂ 3-I 2-CH₃ 1-218C(CH₃)₂CH₂OP(═O)(OCH₃)₂ 3-I 2-CH₃ 1-219 CH(CH₃)CH₂OP(═O)(OC₂H₅)₂ 3-I2-CH₃ 1-220 C(CH₃)₂CH₂OP(═O)(OC₂H₅)₂ 3-I 2-CH₃ 1-221CH(CH₃)CH₂OP(═S)(OCH₃)₂ 3-I 2-CH₃ 1-222 C(CH₃)₂CH₂OP(═S)(OCH₃)₂ 3-I2-CH₃ 1-223 CH(CH₃)CH₂OP(═S)(OC₂H₅)₂ 3-I 2-CH₃ 1-224C(CH₃)₂CH₂OP(═S)(OC₂H₅)₂ 3-I 2-CH₃ 1-225 CH(CH₃)CH₂OCH₃ 3-I 2-Cl 1-226C(CH₃)₂CH₂OCH₃ 3-I 2-Cl 1-227 CH(CH₃)CH₂OC₂H₅ 3-I 2-Cl 1-228C(CH₃)₂CH₂OC₂H₅ 3-I 2-Cl 1-229 CH(CH₃)(CH₂)₂OCH₃ 3-I 2-Cl 1-230C(CH₃)₂(CH₂)₂OCH₃ 3-I 2-Cl 1-231 C(CH₃)₂(CH₂)₃OCH₃ 3-I 2-Cl 1-232C(CH₃)₂(CH₂)₄OCH₃ 3-I 2-Cl 1-233 C(CH₃)₂CH₂OP(═S)(OCH₃)₂ 3-I 2-Cl 1-234CH(CH₃)CH₂OP(═S)(OC₂H₅)₂ 3-I 2-Cl 1-235 C(CH₃)₂CH₂OP(═S)(OC₂H₅)₂ 3-I2-Cl 1-236 CH(CH₃)CH₂NHOOCH₃ 3-I 2-CH₃ 1-237 C(CH₃)₂CH₂NHCOCH₃ 3-I 2-CH₃1-238 CH(CH₃)CH₂N(CH₃)COCH₃ 3-I 2-CH₃ 1-239 C(CH₃)₂CH₂N(CH₃)COCH₃ 3-I2-CH₃ 1-240 CH(CH₃)CH₂NHCOC₂H₅ 3-I 2-CH₃ 1-241 C(CH₃)₂CH₂NHCOC₂H₅ 3-I2-CH₃ 1-242 CH(CH₃)CH₂NHCO₂CH₃ 3-I 2-CH₃ 1-243 C(CH₃)₂CH₂NHCO₂CH₃ 3-I2-CH₃ 1-244 CH(CH₃)CH₂NHCO₂C₂H₅ 3-I 2-CH₃ 1-245 C(CH₃)₂CH₂NHCO₂C₂H₅ 3-I2-CH₃ 1-246 CH(CH₃)CH₂NHSO₂CH₃ 3-I 2-CH₃ 1-247 C(CH₃)₂CH₂NHSO₂CH₃ 3-I2-CH₃ 1-248 CH(CH₃)CH₂NHSO₂C₂H₅ 3-I 2-CH₃ 1-249 C(CH₃)₂CH₂NHSO₂C₂H₅ 3-I2-CH₃ 1-250 CH(CH₃)CH₂N(CH₃)SO₂CH₃ 3-I 2-CH₃ 1-251C(CH₃)₂CH₂N(CH₃)SO₂CH₃ 3-I 2-CH₃ 1-252 CH(CH₃)CH₂NHCONHCH₃ 3-I 2-CH₃1-253 C(CH₃)₂CH₂NHCONHCH₃ 3-I 2-CH₃ 1-254 CH(CH₃)CH₂NHCON(CH₃)₂ 3-I2-CH₃ 1-255 C(CH₃)₂CH₂NHCON(CH₃)₂ 3-I 2-CH₃ 1-256CH(CH₃)CH₂N(CH₃)CON(CH₃)₂ 3-I 2-CH₃ 1-257 C(CH₃)₂CH₂N(CH₃)CON(CH₃)₂ 3-I2-CH₃ 1-258 CH(CH₃)CH₂NHCON(C₂H₅)₂ 3-I 2-CH₃ 1-259C(CH₃)₂CH₂NHCON(C₂H₅)₂ 3-I 2-CH₃ 1-260 CH(CH₃)CH₂NHSO₂NHCH₃ 3-I 2-CH₃1-261 C(CH₃)₂CH₂NHSO₂NHCH₃ 3-I 2-CH₃ 1-262 CH(CH₃)CH₂NHSO₂N(CH₃)₂ 3-I2-CH₃ 1-263 C(CH₃)₂CH₂NHSO₂N(CH₃)₂ 3-I 2-CH₃ 1-264CH(CH₃)CH₂NHSO₂N(C₂H₅)₂ 3-I 2-CH₃ 1-265 C(CH₃)₂CH₂NHSO₂N(C₂H₅)₂ 3-I2-CH₃ 1-266 CH(CH₃)CH₂NHP(═O)(OCH₃)₂ 3-I 2-CH₃ 1-267C(CH₃)₂CH₂NHP(═O)(OCH₃)₂ 3-I 2-CH₃ 1-268 CH(CH₃)CH₂N(CH₃)P(═O)(OCH₃)₂3-I 2-CH₃ 1-269 C(CH₃)₂CH₂N(CH₃)P(═O)(OCH₃)₂ 3-I 2-CH₃ 1-270CH(CH₃)CH₂NHP(═S)(OCH₃)₂ 3-I 2-CH₃ 1-271 C(CH₃)₂CH₂NHP(═S)(OCH₃)₂ 3-I2-CH₃ 1-272 CH(CH₃)CH₂NHP(═S)(OC₂H₅)₂ 3-I 2-CH₃ 1-273C(CH₃)₂CH₂NHP(═S)(OC₂H₅)₂ 3-I 2-CH₃ 1-274 CH(CH₃)CH₂NHCOCH₃ 3-I 2-Cl1-275 C(CH₃)₂CH₂NHCOCH₃ 3-I 2-Cl 1-276 CH(CH₃)CH₂NHCO₂C₂H₅ 3-I 2-Cl1-277 C(CH₃)₂CH₂NHCO₂C₂H₅ 3-I 2-Cl 1-278 CH(CH₃)CH₂NHSO₂CH₃ 3-I 2-Cl1-279 C(CH₃)₂CH₂NHSO₂CH₃ 3-I 2-Cl 1-280 CH(CH₃)CH₂NHSO₂N(CH₃)₂ 3-I 2-Cl1-281 C(CH₃)₂CH₂NHSO₂N(CH₃)₂ 3-I 2-Cl 1-282 (CH₂)₂SCH₃ 3-I 2-CH₃ 1-283(CH₂)₃SCH₃ 3-I 2-CH₃ 1-284 (CH₂)₂SC₂H₅ 3-I 2-CH₃ 1-285 (CH₂)₂SC₃H₇-i 3-I2-CH₃ 1-286 CH(CH₃)CH₂SH 3-I 2-CH₃ 1-287 CH(CH₃)CH₂SCH₃ 3-I 2-CH₃ 1-288CH(CH₃)CH₂SOCH₃ 3-I 2-CH₃ 1-289 CH(CH₃)CH₂SO₂CH₃ 3-I 2-CH₃ 1-290C(*)H(CH₃)CH₂SCH₃ 3-I 2-CH₃ 180-183 (S)-enantiomer 1-291C(*)H(CH₃)CH₂SOCH₃ 3-I 2-CH₃ (S)-enantiomer 1-292 C(*)H(CH₃)CH₂SO₂CH₃3-I 2-CH₃ 87-90 (S)-enantiomer 1-293 C(*)H(CH₃)CH₂SCH₃ 3-I 2-CH₃(R)-enantiomer 1-294 C(*)H(CH₃)CH₂SOCH₃ 3-I 2-CH₃ (R)-enantiomer 1-295C(*)H(CH₃)CH₂SO₂CH₃ 3-I 2-CH₃ (R)-enantiomer 1-296 C(CH₃)₂CH₂SCH₃ 3-I2-CH₃ 216-217 1-297 C(CH₃)₂CH₂SOCH₃ 3-I 2-CH₃ 85-89 1-298C(CH₃)₂CH₂SO₂CH₃ 3-I 2-CH₃ 115-118 1-299 CH(CH₃)CH₂SC₂H₅ 3-I 2-CH₃ 1-300CH(CH₃)CH₂SOC₂H₅ 3-I 2-CH₃ 1-301 CH(CH₃)CH₂SO₂C₂H₅ 3-I 2-CH₃ 1-302C(*)H(CH₃)CH₂SC₂H₅ 3-I 2-CH₃ (S)-enantiomer 1-303 C(*)H(CH₃)CH₂SOC₂H₅3-I 2-CH₃ (S)-enantiomer 1-304 C(*)H(CH₃)CH₂SO₂C₂H₅ 3-I 2-CH₃(S)-enantiomer 1-305 C(*)H(CH₃)CH₂SC₂H₅ 3-I 2-CH₃ (R)-enantiomer 1-306C(*)H(CH₃)CH₂SOC₂H₅ 3-I 2-CH₃ (R)-enantiomer 1-307 C(*)H(CH₃)CH₂SO₂C₂H₅3-I 2-CH₃ (R)-enantiomer 1-308 C(CH₃)₂CH₂SC₂H₅ 3-I 2-CH₃ 1-309C(CH₃)₂CH₂SOC₂H₅ 3-I 2-CH₃ 1-310 C(CH₃)₂CH₂SO₂C₂H₅ 3-I 2-CH₃ 1-311CH(CH₃)CH₂SC₃H₇-n 3-I 2-CH₃ 1-312 CH(CH₃)CH₂SC₃H₇-i 3-I 2-CH₃ 1-313CH(CH₃)CH₂SCH₂CH═CH₂ 3-I 2-CH₃ 1-314 CH(CH₃)CH₂SCH₂C≡CH 3-I 2-CH₃ 1-315CH(CH₃)(CH₂)₂SCH₃ 3-I 2-CH₃ 1-316 C(CH₃)₂(CH₂)₂SCH₃ 3-I 2-CH₃ 1-317CH(CH₃)(CH₂)₃SCH₃ 3-I 2-CH₃ 1-318 C(CH₃)₂(CH₂)₃SCH₃ 3-I 2-CH₃ 1-319CH(CH₃)(CH₂)₄SCH₃ 3-I 2-CH₃ 1-320 C(CH₃)₂(CH₂)₄SCH₃ 3-I 2-CH₃ 1-321CH(C₂H₅)(CH₂)₂SCH₃ 3-I 2-CH₃ 1-322 CH(CH₃)CH₂SCH₂CF₃ 3-I 2-CH₃ 1-323CH(CH₃)CH₂SCH₂CN 3-I 2-CH₃ 1-324 CH(CH₃)CH₂S(CH₂)₂OCH₃ 3-I 2-CH₃ 1-325CH(CH₃)CH₂S(CH₂)₂SCH₃ 3-I 2-CH₃ 1-326 CH(CH₃)CH₂SCH₂CO₂N(CH₃)₂ 3-I 2-CH₃1-327 CH(CH₃)CH₂SCH₂CO₂N(C₂H₅)₂ 3-I 2-CH₃ 1-328 CH(CH₃)CH₂SCH₂Ph 3-I2-CH₃ 1-329 CH(CH₃)CH₂S-Ph 3-I 2-CH₃ 1-330 C(CH₃)₂CH₂S-Ph 3-I 2-CH₃1-331 CH(CH₃)CH₂S-2-Pyr 3-I 2-CH₃ 1-332 C(CH₃)₂CH₂S-2-Pyr 3-I 2-CH₃1-333 CH(CH₃)CH₂S-3-Pyr 3-I 2-CH₃ 1-334 C(CH₃)₂CH₂S-3-Pyr 3-I 2-CH₃1-335 CH(CH₃)CH₂S-4-Pyr 3-I 2-CH₃ 1-336 C(CH₃)₂CH₂S-4-Pyr 3-I 2-CH₃1-337 CH(Ph)CH₂SCH₃ 3-I 2-CH₃ 1-338 CH(CH₃)CH₂SCOCH₃ 3-I 2-CH₃ 1-339CH(CH₃)CH₂SCONHCH₃ 3-I 2-CH₃ 1-340 C(CH₃)₂CH₂SCONHCH₃ 3-I 2-CH₃ 1-341CH(CH₃)CH₂SCON(C₂H₅)₂ 3-I 2-CH₃ 1-342 C(CH₃)₂CH₂SCON(C₂H₅)₂ 3-I 2-CH₃1-343 CH(CH₃)CH₂SC(═S)NHCH₃ 3-I 2-CH₃ 1-344 C(CH₃)₂CH₂SC(═S)NHCH₃ 3-I2-CH₃ 1-345 CH(CH₃)CH₂SC(═S)N(C₂H₅)₂ 3-I 2-CH₃ 1-346C(CH₃)₂CH₂SC(═S)N(C₂H₅)₂ 3-I 2-CH₃ 1-347 CH(CH₃)CH₂S—SCH₃ 3-I 2-CH₃1-348 C(CH₃)₂CH₂S—SCH₃ 3-I 2-CH₃ 1-349 CH(CH₃)CH₂SO₂NH₂ 3-I 2-CH₃ 1-350C(CH₃)₂CH₂SO₂NH₂ 3-I 2-CH₃ 1-351 CH(CH₃)CH₂SO₂NHCH₃ 3-I 2-CH₃ 1-352C(CH₃)₂CH₂SO₂NHCH₃ 3-I 2-CH₃ 1-353 CH(CH₃)CH₂SO₂NHC₂H₅ 3-I 2-CH₃ 1-354C(CH₃)₂CH₂SO₂NHC₂H₅ 3-I 2-CH₃ 1-355 CH(CH₃)CH₂SO₂N(CH₃)₂ 3-I 2-CH₃ 1-356C(CH₃)₂CH₂SO₂N(CH₃)₂ 3-I 2-CH₃ 1-357 CH(CH₃)CH₂SO₂N(C₂H₅)₂ 3-I 2-CH₃1-358 C(CH₃)₂CH₂SO₂N(C₂H₅)₂ 3-I 2-CH₃ 1-359 CH(CH₃)CH₂S(═O)OCH₃ 3-I2-CH₃ 1-360 C(CH₃)₂CH₂S(═O)OCH₃ 3-I 2-CH₃ 1-361 CH(CH₃)CH₂S(═O)OC₂H₅ 3-I2-CH₃ 1-362 C(CH₃)₂CH₂S(═O)OC₂H₅ 3-I 2-CH₃ 1-363CH(CH₃)CH₂S(CH₃)═N—SO₂CH₃ 3-I 2-CH₃ 1-364 C(CH₃)₂CH₂S(CH₃)═N—SO₂CH₃ 3-I2-CH₃ 1-365 CH(CH₃)CH₂S(CH₃)═N—SO₂Ph 3-I 2-CH₃ 1-366C(CH₃)₂CH₂S(CH₃)═N—SO₂Ph 3-I 2-CH₃ 1-367 CH(CH₃)CH₂S⁺(CH₃)₂I⁻ 3-I 2-CH₃1-368 C(CH₃)₂CH₂S⁺(CH₃)₂I⁻ 3-I 2-CH₃ 1-369 CH(CH₃)CH₂SCH₃ 3-I 2-Cl 1-370CH(CH₃)CH₂SOCH₃ 3-I 2-Cl 1-371 CH(CH₃)CH₂SO₂CH₃ 3-I 2-Cl 1-372C(CH₃)₂CH₂SCH₃ 3-I 2-Cl 170-173 1-373 C(CH₃)₂CH₂SOCH₃ 3-I 2-Cl 83-871-374 C(CH₃)₂CH₂SO₂CH₃ 3-I 2-Cl 196-198 1-375 CH(CH₃)CH₂SC₂H₅ 3-I 2-Cl1-376 CH(CH₃)CH₂SOC₂H₅ 3-I 2-Cl 1-377 CH(CH₃)CH₂SO₂C₂H₅ 3-I 2-Cl 1-378C(CH₃)₂CH₂SC₂H₅ 3-I 2-Cl 1-379 C(CH₃)₂CH₂SOC₂H₅ 3-I 2-Cl 1-380C(CH₃)₂CH₂SO₂C₂H₅ 3-I 2-Cl 1-381 CH(CH₃)(CH₂)₂SCH₃ 3-I 2-Cl 1-382C(CH₃)₂(CH₂)₂SCH₃ 3-I 2-Cl 1-383 CH(CH₃)(CH₂)₃SCH₃ 3-I 2-Cl 1-384C(CH₃)₂(CH₂)₃SCH₃ 3-I 2-Cl 1-385 CH(CH₃)(CH₂)₄SCH₃ 3-I 2-Cl 1-386C(CH₃)₂(CH₂)₄SCH₃ 3-I 2-Cl 1-387 CH(CH₃)CH₂SO₂NH₂ 3-I 2-Cl 1-388CH(CH₃)CH₂SO₂NHCH₃ 3-I 2-Cl 1-389 CH(CH₃)CH₂SO₂NHC₂H₅ 3-I 2-Cl 1-390CH(CH₃)CH₂SO₂N(CH₃)₂ 3-I 2-Cl 1-391 CH(CH₃)CH₂SO₂N(C₂H₅)₂ 3-I 2-Cl 1-392CH(CH₃)CH₂P(═O)(OCH₃)₂ 3-I 2-CH₃ 1-393 C(CH₃)₂CH₂P(═O)(OCH₃)₂ 3-I 2-CH₃1-394 CH(CH₃)CH₂P(═O)(OC₂H₅)₂ 3-I 2-CH₃ 1-395 C(CH₃)₂CH₂P(═O)(OC₂H₅)₂3-I 2-CH₃ 1-396 C(CH₃)₂CH₂SCH₃ H 2-CH₃ 1-397 C(CH₃)₂CH₂SCH₃ 3-F 2-CH₃1-398 C(CH₃)₂CH₂SCH₃ 3-Cl 2-CH₃ 1-399 C(CH₃)₂CH₂SOCH₃ 3-Cl 2-CH₃ 1-400C(CH₃)₂CH₂SO₂CH₃ 3-Cl 2-CH₃ 1-401 C(CH₃)₂CH₂SCH₃ 3-Br 2-CH₃ 1-402C(CH₃)₂CH₂SOCH₃ 3-Br 2-CH₃ 1-403 C(CH₃)₂CH₂SO₂CH₃ 3-Br 2-CH₃ 1-404C(CH₃)₂CH₂SCH₃ 3. 4-Cl₂ 2-CH₃ 1-405 C(CH₃)₂CH₂SCH₃ 4-Cl 2-CH₃ 1-406C(CH₃)₂CH₂SCH₃ 4-Br 2-CH₃ 1-407 C(CH₃)₂CH₂SCH₃ 4-I 2-CH₃ 1-408C(CH₃)₂CH₂SCH₃ 4-Cl 2-CH₃ 1-409 C(CH₃)₂CH₂SCH₃ 3-CH₃ 2-CH₃ 1-410C(CH₃)₂CH₂SCH₃ 3-C₂H₅ 2-CH₃ 1-411 C(CH₃)₂CH₂SCH₃ 3-i-C₃H₇ 2-CH₃ 1-412C(CH₃)₂CH₂SCH₃ 3-CF₃ 2-CH₃ 1-413 C(CH₃)₂CH₂SCH₃ 3-CH═CH₂ 2-CH₃ 1-414C(CH₃)₂CH₂SCH₃ 3-C≡CH 2-CH₃ 1-415 C(CH₃)₂CH₂SCH₃ 3-C≡CC(CH₃)₃ 2-CH₃1-416 C(CH₃)₂CH₂SCH₃ 3-C≡CCF₃ 2-CH₃ 1-417 C(CH₃)₂CH₂SCH₃ 3-NO₂ 2-CH₃1-418 C(CH₃)₂CH₂SCH₃ 3-NH₂ 2-CH₃ 1-419 C(CH₃)₂CH₂SCH₃ 3-N(CH₃)₂ 2-CH₃1-420 C(CH₃)₂CH₂SCH₃ 3-NHCOCH₃ 2-CH₃ 1-421 C(CH₃)₂CH₂SCH₃ 3-NHCOCF₃2-CH₃ 1-422 C(CH₃)₂CH₂SCH₃ 3-NHCO₂CH₃ 2-CH₃ 1-423 C(CH₃)₂CH₂SCH₃3-NHSO₂CH₃ 2-CH₃ 1-424 C(CH₃)₂CH₂SCH₃ 3-NHSO₂CF₃ 2-CH₃ 1-425C(CH₃)₂CH₂SCH₃ 3-OCH₃ 2-CH₃ 1-426 C(CH₃)₂CH₂SCH₃ 3-OCF₃ 2-CH₃ 1-427C(CH₃)₂CH₂SCH₃ 3-OCOCH₃ 2-CH₃ 1-428 C(CH₃)₂CH₂SCH₃ 3-OCOCF₃ 2-CH₃ 1-429C(CH₃)₂CH₂SCH₃ 3-OCONHCH₃ 2-CH₃ 1-430 C(CH₃)₂CH₂SCH₃ 3-OCON(CH₃)₂ 2-CH₃1-431 C(CH₃)₂CH₂SCH₃ 3-SCH₃ 2-CH₃ 1-432 C(CH₃)₂CH₂SCH₃ 3-SOCH₃ 2-CH₃1-433 C(CH₃)₂CH₂SCH₃ 3-SO₂CH₃ 2-CH₃ 1-434 C(CH₃)₂CH₂SCH₃ 3-SCF₃ 2-CH₃1-435 C(CH₃)₂CH₂SCH₃ 3-SOCF₃ 2-CH₃ 1-436 C(CH₃)₂CH₂SCH₃ 3-SO₂CF₃ 2-CH₃1-437 C(CH₃)₂CH₂SCH₃ 3-OSO₂CH₃ 2-CH₃ 1-438 C(CH₃)₂CH₂SCH₃ 3-OSO₂CF₃2-CH₃ 1-439 C(CH₃)₂CH₂SCH₃ 3-CH═CHCH═CH-4 2-CH₃ 1-440 C(CH₃)₂CH₂SCH₃3-OCH₂O-4 2-CH₃ 1-441 C(CH₃)₂CH₂SCH₃ 3-OCF₂O-4 2-CH₃ 1-442C(CH₃)₂CH₂SCH₃ 3-OCF₂CF₂O-4 2-CH₃ 1-443 C(CH₃)₂CH₂SCH₃ H 2-Cl 1-444C(CH₃)₂CH₂SCH₃ 3-F 2-Cl 1-445 C(CH₃)₂CH₂SCH₃ 3-Cl 2-Cl 1-446C(CH₃)₂CH₂SOCH₃ 3-Cl 2-Cl 1-447 C(CH₃)₂CH₂SO₂CH₃ 3-Cl 2-Cl 1-448C(CH₃)₂CH₂SCH₃ 3-Br 2-Cl 1-449 C(CH₃)₂CH₂SOCH₃ 3-Br 2-Cl 1-450C(CH₃)₂CH₂SO₂CH₃ 3-Br 2-Cl 1-451 C(CH₃)₂CH₂SCH₃ 3,4-Cl₂ 2-Cl 1-452C(CH₃)₂CH₂SCH₃ 3-CF₃ 2-Cl 1-453 C(CH₃)₂CH₂SCH₃ 3-NO₂ 2-Cl 1-454C(CH₃)₂CH₂SCH₃ 3-OCF₃ 2-Cl 1-455 C(CH₃)₂CH₂SCH₃ 3-SCF₃ 2-Cl 1-456C(CH₃)₂CH₂SCH₃ 3-OSO₂CH₃ 2-Cl 1-457 C(CH₃)₂CH₂SCH₃ 3-OSO₂CF₃ 2-Cl 1-458C(CH₃)₂CH₂SCH₃ 3-I H 231-232 1-459 C(CH₃)₂CH₂SCH₃ 3-I H 119-122 1-460C(CH₃)₂CH₂SCH₃ 3-I H 118-121 1-461 C(CH₃)₂CH₂SCH₃ 3-I 3-CH₃ 1-462CH(CH₃)CH₂SCH₃ 3-I 2,3-(CH₃)₂ 1-463 CH(CH₃)CH₂SCH₃ 3-I 2,5-(CH₃)₂ 1-464CH(CH₃)CH₂SCH₃ 3-I 2,6-(CH₃)₂ 1-465 CH(CH₃)CH₂SCH₃ 3-I 2-(CH₂)₃-3 1-466CH(CH₃)CH₂SCH₃ 3-I 2-(CH₂)₄-3 1-467 C(CH₃)₂CH₂SCH₃ 3-I 2-C₂H₅ 1-468C(CH₃)₂CH₂SCH₃ 3-I 2-n-C₃H₇ 1-469 C(CH₃)₂CH₂SCH₃ 3-I 2-i-C₃H₇ 1-470C(CH₃)₂CH₂SCH₃ 3-I 2-t-C₄H₉ 1-471 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂OH 1-472C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂OCH₃ 1-473 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂SCH₃ 1-474C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂SOCH₃ 1-475 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂SO₂CH₃ 1-476C(CH₃)₂CH₂SCH₃ 3-I 2-Ph 1-477 C(CH₃)₂CH₂SCH₃ 3-I 2-F 1-478C(CH₃)₂CH₂SCH₃ 3-I 2-Cl-3-F 1-479 C(CH₃)₂CH₂SCH₃ 3-I 2,3-Cl₂ 1-480C(CH₃)₂CH₂SCH₃ 3-I 2,5-Cl₂ 1-481 C(CH₃)₂CH₂SCH₃ 3-I 2-Br 1-482C(CH₃)₂CH₂SCH₃ 3-I 2-I 1-483 C(CH₃)₂CH₂SCH₃ 3-I 2-CF₃ 1-484C(CH₃)₂CH₂SCH₃ 3-I 2-CHO 1-485 C(CH₃)₂CH₂SCH₃ 3-I 2-COCH₃ 1-486C(CH₃)₂CH₂SCH₃ 3-I 2-CN 1-487 C(CH₃)₂CH₂SCH₃ 3-I 2-CF₃ 1-488C(CH₃)₂CH₂SCH₃ 3-I 2-OCH₃ 1-489 C(CH₃)₂CH₂SCH₃ 3-I 2-OCF₃ 1-490CH(CH₃)CH₂SCH₃ 3-I 2-OCH₂O-3 1-491 CH(CH₃)CH₂SCH₃ 3-I 2-OCF₂O-3 1-492C(CH₃)₂CH₂SCH₃ 3-I 2-SCH₃ 1-493 C(CH₃)₂CH₂SCH₃ 3-I 2-NO₂ 1-494C(CH₃)₂CH₂SCH₃ 3-I 2-N(CH₃)₂ 1-495 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-3-F 1-496C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-5-F 1-497 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-3-Cl 1-498C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-5-Cl 1-499 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-3-OH 1-500C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-3-OCH₃

TABLE 2 General formula (I-3) (I-3)

No. R¹ R² R³ Xm Yn Melting point (° C.) 2-1  CH₃ CH₃ H 3-I 2-CH₃ 2-2 C₂H₅ CH₃ H 3-I 2-CH₃ 2-3  C₂H₅ C₂H₅ H 3-I 2-CH₃ 2-4  C₂H₅ C₂H₅ H 3-I2-Cl 2-5  n-C₃H₇ CH₃ H 3-I 2-CH₃ 2-6  n-C₃H₇ C₂H₅ H 3-I 2-CH₃ 2-7 n-C₃H₇ n-C₃H₇ H 3-I 2-CH₃ 2-8  i-C₃H₇ CH₃ H 3-I 2-CH₃ 2-9  i-C₃H₇ C₂H₅ H3-I 2-CH₃ 2-10 i-C₃H₇ H CH₃ 3-I 2-CH₃ 2-11 i-C₃H₇ COCH₃ CH₃ 3-I 2-CH₃2-12 i-C₃H₇ H C₂H₅ 3-I 2-CH₃ 2-13 i-C₃H₇ CH₃ CH₃ 3-I 2-CH₃ 2-14 i-C₃H₇CH₃ COCH₃ 3-I 2-CH₃ 2-15 i-C₃H₇ CH₃ H 3-I 2-Cl 2-16 i-C₃H₇ H CH₃ 3-I2-Cl 2-17 CH₂CH₂SCH₃ CH₃ H 3-I 2-CH₃ 2-18 CH₂CH₂SCH₃ C₂H₅ H 3-I 2-CH₃2-19 CH(CH₃)CH₂SCH₃ H CH₃ 3-I 2-CH₃ 2-20 CH(CH₃)CH₂SOCH₃ H CH₃ 3-I 2-CH₃2-21 CH(CH₃)CH₂SO₂CH₃ H CH₃ 3-I 2-CH₃ 2-22 C(CH₃)₂CH₂SCH₃ H CH₃ 3-I H2-23 C(CH₃)₂CH₂SOCH₃ H CH₃ 3-I H 2-24 C(CH₃)₂CH₂SO₂CH₃ H CH₃ 3-I H 2-22C(CH₃)₂CH₂SCH₃ H C₂H₅ 3-I H 54-56 2-23 C(CH₃)₂CH₂SOCH₃ H C₂H₅ 3-I H86-88 2-24 C(CH₃)₂CH₂SO₂CH₃ H C₂H₅ 3-I H 81-83 2-25 C(CH₃)₂CH₂SCH₃ H CH₃3-I 2-CH₃ 2-26 C(CH₃)₂CH₂SOCH₃ H CH₃ 3-I 2-CH₃ 2-27 C(CH₃)₂CH₂SO₂CH₃ HCH₃ 3-I 2-CH₃ 2-28 C(CH₃)₂CH₂SCH₃ H C₂H₅ 3-I 2-CH₃ 2-29 C(CH₃)₂CH₂SOCH₃H C₂H₅ 3-I 2-CH₃ 2-30 C(CH₃)₂CH₂SO₂CH₃ H C₂H₅ 3-I 2-CH₃ 2-31CH(CH₃)CH₂SC₂H₅ H CH₃ 3-I 2-CH₃ 2-32 CH(CH₃)CH₂SOC₂H₅ H CH₃ 3-I 2-CH₃2-33 CH(CH₃)CH₂SO₂C₂H₅ H CH₃ 3-I 2-CH₃ 2-34 CH(CH₃)CH₂SCH₃ H CH₃ 3-I2-Cl 2-35 CH(CH₃)CH₂SOCH₃ H CH₃ 3-I 2-Cl 2-36 CH(CH₃)CH₂SO₂CH₃ H CH₃ 3-I2-Cl 2-37 C(CH₃)₂CH₂SCH₃ H CH₃ 3-I 2-Cl 2-38 C(CH₃)₂CH₂SOCH₃ H CH₃ 3-I2-Cl 2-39 C(CH₃)₂CH₂SO₂CH₃ H CH₃ 3-I 2-Cl 2-40 CH(CH₃)CH₂SC₂H₅ H CH₃ 3-I2-Cl 2-41 CH(CH₃)CH₂SOC₂H₅ H CH₃ 3-I 2-Cl 2-42 CH(CH₃)CH₂SO₂C₂H₅ H CH₃3-I 2-Cl

TABLE 3 General formula (I-4) (I-4)

(R² = R³ = H) Melting No. R¹ Xm Yn point (° C.) 3-1  i-C₃H₇ 3-I H 3-2 CH(CH₃)CH₂SCH₃ 3-I H 3-3  CH(CH₃)CH₂SOCH₃ 3-I H 3-4  CH(CH₃)CH₂SO₂CH₃3-I H 3-5  C(CH₃)₂CH₂SCH₃ 3-I H 170-171 3-6  C(CH₃)₂CH₂SOCH₃ 3-I H115-118 3-7  C(CH₃)₂CH₂SO₂CH₃ 3-I H 120-123 3-8  CH(CH₃)CH₂SCH₃ 3-I2-CH₃ 3-9  C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃ 3-10 CH(CH₃)CH₂SCH₃ 3-I 6-CH₃ 3-11C(CH₃)₂CH₂SCH₃ 3-I 6-CH₃ 3-12 CH(CH₃)CH₂SCH₃ 3-I 2-C₂H₅ 3-13C(CH₃)₂CH₂SCH₃ 3-I 2-C₂H₅ 3-14 CH(CH₃)CH₂SCH₃ 3-I 6-C₂H₅ 3-15C(CH₃)₂CH₂SCH₃ 3-I 6-C₂H₅ 3-16 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂SCH₃ 3-17C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂SOCH₃ 3-18 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₂SO₂CH₃ 3-19C(CH₃)₂CH₂SCH₃ 3-I 6-CH₂SCH₃ 3-20 C(CH₃)₂CH₂SCH₃ 3-I 6-CH₂SOCH₃ 3-21C(CH₃)₂CH₂SCH₃ 3-I 6-CH₂SO₂CH₃ 3-22 C(CH₃)₂CH₂SCH₃ 3-I 2-F 3-23C(CH₃)₂CH₂SCH₃ 3-I 6-F 3-24 C(CH₃)₂CH₂SCH₃ 3-I 2-Cl 205 3-25C(CH₃)₂CH₂SOCH₃ 3-I 2-Cl 3-26 C(CH₃)₂CH₂SO₂CH₃ 3-I 2-Cl 204 3-27C(CH₃)₂CH₂SCH₃ 3-I 4-Cl 3-28 C(CH₃)₂CH₂SCH₃ 3-I 6-Cl 221 3-29C(CH₃)₂CH₂SCH₃ 3-I 2-Br 3-30 C(CH₃)₂CH₂SCH₃ 3-I 4-Br 3-31 C(CH₃)₂CH₂SCH₃3-I 6-Br 3-32 C(CH₃)₂CH₂SCH₃ 3-I 2-I 3-33 C(CH₃)₂CH₂SCH₃ 3-I 4-I 3-34C(CH₃)₂CH₂SCH₃ 3-I 6-I 3-35 C(CH₃)₂CH₂SCH₃ 3-I 2-CN 3-36 C(CH₃)₂CH₂SCH₃3-I 6-CN 3-37 C(CH₃)₂CH₂SCH₃ 3-I 2,4-Cl₂ 3-38 C(CH₃)₂CH₂SCH₃ 3-I 4,6-Cl₂3-39 C(CH₃)₂CH₂SCH₃ 3-I 2,4-Br₂ 3-40 C(CH₃)₂CH₂SCH₃ 3-I 2-Cl-4-Br 3-41C(CH₃)₂CH₂SCH₃ 3-I 2-Cl-4-I 3-42 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-4-Cl 3-43C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-4-Br 3-44 C(CH₃)₂CH₂SCH₃ 3-I 2-CH₃-4-I

Followings are typical examples of the present invention, but thepresent invention is not limited thereto.

EXAMPLE 1 Production ofN¹-(2-chloro-4-pentafluorosulfanylphenyl)-N²-(1,1-dimethyl-2-methylthioethyl)-3-iodophthalamide (Compound No. 1-372)

750 mg (2.0 mmol) of N-(1,1-dimethyl-2-methylthioethyl)-6-iodophthalicacid isoimide was dissolved in 10 ml of acetonitrile, 510 mg (2.0 mmol)of 2-chloro-4-pentafluorosulfanylaniline and 10 mg of trifluoroaceticacid were added, and the mixture was stirred under room temperature for2 hours. Precipitated crystals were collected by filtration and washedwith a small amount of ether to obtain 1.0 g of the intended product.

Yield: 79%

Physical property: melting point 170 to 173° C.

Example 2 Production ofN¹-(2-chloro-4-pentafluorosulfanylphenyl)-N²-(1,1-dimethyl-2-methylsulfonylethyl)-3-iodophthalamide (Compound No. 1-374)

0.63 g (1.0 mmol) ofN¹-(2-chloro-4-pentafluorosulfanylphenyl)-N²-(1,1-dimethyl-2-methylthioethyl)-3-iodophthalamide was dissolved in 10 ml of chloroform, andthe mixture was cooled to 0° C. To the solution, 0.38 g (2.2 mmol) ofmetachloroperbenzoic acid was added. After stirring for 1 hour, thereaction mixture solution was washed with an aqueous sodium thiosulfatesolution and a 10% aqueous potassium carbonate solution, dried overanhydrous magnesium sulfate, and the solvent was distilled off under areduced pressure to obtain 0.55 g of the intended product.

Yield: 84%

Physical property: melting point 196 to 198° C.

The agrohorticultural insecticides containing a phthalamide derivativerepresented by the general formula (I) of the present invention as anactive ingredient, are suitable for controlling various insect pestssuch as agrohorticultural insect pests, stored grain insect pests,sanitary insect pests, nematodes, etc., which are injurious to paddyrice, fruit trees, vegetables, other crops, flowers, ornamental plants,etc. They have a marked insecticidal effect, for example, on LEPIDOPTERAincluding summer fruit tortrix (Adoxophyes orana fasciata), smaller teatortrix (Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata),oriental fruit moth (Grapholita molesta), soybean pod border(Leguminivora glycinivorella), mulberry leafroller (Olethreutesmori),tea leafroller (Caloptiliathevivora), Caloptilia sp. (Caloptiliazachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer(Spulerrina astaurota), common white (Piers rapae crucivora), tobaccobudworm (Heliothis sp.), codling moth (Laspey resia pomonella),diamondback moth (Plutella xylostella), apple fruit moth (Argyresthiaconjugella), peach fruit moth (Carposina niponensis), rice stem borer(Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis),tobacco moth (Ephestia elutelia), mulberry pyralid (Glyphodes pyloalis),yellow rice borer (Scirpophaga incertulas), rice skipper (Parnaraguttata), rice armyworm (Pseudaletia separata), pink borer (SesamIainferens), common cutworm (Spodoptera litura), beet armyworm (Spodopteraegigua), etc.; HEMIPTERA including aster leafhopper (Macrostelesfascifrons), green rice leafhopper (Nephotettix cincticepts), brown riceplanthopper (Nilaparvata lugens), whitebacked rice planthopper(Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly(Aleurolobus taonabae), sweetpotato whitefly (Bemisia tabaci),greenhouse whitefly (Trialeurodes vaporariorum), turnup aphid (Lipaphiserysimi), green peach aphid (Myzus persicae), Indian wax scale(Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii),camphor scale (Pseudaonidia duplex), san Jose scale (Comstockaspisperniciosa), arrowhead scale (Unaspis yanonensis), etc.; TYLENCHIDAincluding root-lesion nematode (Pratylenchus sp.), soybean beetle(Anomala rufocuprea), Japanese beetle (Popilla japonica), tobacco beetle(Lasioderma serricorne), powderpost beetle (Lyctus brunneus),twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), azuki beanweevil (Callosobruchus chinensis), vegetable weevil (Listroderescostirostris), maize weevil (Sitophilus zeamais), boll weevil(Anthonomus grandis grandis), rice water weevil (Lissorhoptrusoryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leafbeetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata),pine shoot beetle (Tomicus piniperda), Colorado potato beetle(Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis),corn rootworm (Diabrotica sp.), etc. DIPTERA including Coquillet melonfly (Dacus (Zeugodacus) cucurbitae), oriental fruit fly(Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae), onionmaggot (Delia antiqua), seedcorn maggot (Delia platura), soybean podgall midge (Asphondylis sp.), muscid fly (Musca domestica), housemosquito (Culex pipiens pipiens), etc.; TYLENCHIDA including coffeeroot-lesion nematode (Pratylenchus coffeae), potato cyst nematode(Glabodera rostchiensis), root-knot nematode (Meloidogyne sp.), citrusnematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchusavenae), chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.; andACARINA including citrus red mite (Panonychus citri), fruit tree redspider mite (Panonychus uimi), carmine spider mite (Tetranychuscinnabarinus), Kanzawa spider mite (Tetranychus KanzawaI Kishida),two-spotted spider mite (Tetranychus urticae Koch), pink tea rust mite(Acaphylla theae), pink citrus rust mite (Aculops pelekassi), purple teamice (Calacarus carinatus), pear rust mite (Epitrimerus pyri), etc.

The agrohorticultural insecticide, which contains as an activeingredient the phthalamide derivative of the general formula (I) of thepresent invention has a marked insecticidal effect on the above-typicalinsect pests injurious to paddy field crops, upland crops, fruit trees,vegetables, other crops, flowers and ornamental plants, and the like.Therefore, the desired effect of the agrohorticultural insecticide ofthe present invention can be obtained by applying the presentagrohorticultural insecticide to the nursery facility; paddy field;upland field; seeds or stalks and leaves of fruits, vegetables, othercrops, flowers and ornamental plants; cultural medium such as paddyfield water, soil, etc.; at a season at which the insect pests areexpected to appear, before their appearance or at the time when theirappearance is confirmed. Particularly, a preferable application forusing the agrohorticultural insecticide of the present invention is theapplication for which so-called “penetration and translocation” areutilized, wherein the present agrohorticultural insecticide is appliedto the nursery soil of crops, flowers and ornamental plants or the like;the picking-in hole soil at a transplantation; the plant roots; theirrigation water; or the cultural water of a water culture; so as touptake the compound of the present application from the roots through ornot through the soil.

The agrohorticultural insecticide of the present invention is generallyprepared into conveniently usable forms according to an ordinary mannerfor preparation of agrochemicals.

That is, the phthalamide derivative represented by the general formula(I) and, optionally, an adjuvant are blended with a suitable inertcarrier in a proper proportion and prepared into a suitable preparationform such as a suspension, emulsifiable concentrate, solubleconcentrate, wettable powder, granulated wettable powder, granules,dust, tablets, pack or the like through dissolution, dispersion,suspension, mixing, impregnation, adsorption, or sticking.

The inert carrier usable in the present invention may be either solid orliquid. As a material usable as the solid carrier, it includes soybeanflour, cereal flour, wood flour, bark flour, saw dust, powdered tobaccostalks, powdered walnut shells, bran, powdered cellulose, extractionresidue of vegetables, synthetic polymers such as powdered syntheticresins, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talcand pyrophyllite), silicas (e.g. diatomaceous earth, silica sand, mica,andwhite carbon [synthetic, high-dispersion silicic acid, also calledfinely divided hydrated silica or hydrated silicic acid, some ofcommercially available products contain calcium silicate as the majorcomponent]), activated carbon, powdered sulfur, pumice, calcineddiatomaceous earth, ground brick, fly ash, sand, calcium carbonate,calcium phosphate and other inorganic or mineral powders, plasticsupports such as polyethylene, polypropylene, poly (vinylidenechloride), chemical fertilizers such as ammonium sulfate, ammoniumphosphate, ammonium nitrate, urea, and ammonium chloride, and compost.These carriers may be used alone or as a mixture thereof.

A material usable as the liquid carrier is selected from materials thathave solubility in themselves or which are without such solubility butare capable of dispersing an active ingredient with the aid of anadjuvant. The following are typical examples of the liquid carrier andcan be used alone or as a mixture thereof: water, alcohols (e.g.methanol, ethanol, isopropanol, butanol, and ethylene glycol), ketones(e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutylketone, and cyclohexanone), ethers (e.g. ethyl ether, dioxane,Cellosolve, dipropyl ether, and tetrahydrofuran), aliphatic hydrocarbon(e.g. kerosene and mineral oils), aromatic hydrocarbons (e.g. benzene,toluene, xylene, solvent naphtha, and alkyl-naphthalenes), halogenatedhydrocarbons (e.g. dichloroethane, chloroform, carbon tetrachloride, andchlorobenzene), esters (e.g. ethyl acetate, diisopropyl phthalate,dibutyl phthalate, and dioctyl phthalate), amides (e.g.dimethylformamide, diethylformamide, and dimethylacetamide), nitriles(e.g. acetonitrile), and dimethyl sulfoxide.

The following are typical examples of other adjuvants, which are useddepending upon purposes and used alone or in combination thereof in somecases, or need not be used at all.

To emulsify, disperse, dissolve and/or wet a compound as activeingredient, a surfactant is used. Examples of the surfactants includepolyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers,polyoxyethylene higher fatty acid esters, polyoxyethylene resonates,polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitanmonooleate, alkylarylsulfonates, naphthalene sulfonic acid condensationproducts, ligninsulfonates, and higher alcohol sulfate esters.

Further, to stabilize the dispersion of a compound as active ingredient,tackify it and/or bind it, the adjuvants exemplified below may also beused, namely, there may also be used adjuvants such as casein, gelatin,starch, methyl cellulose, carboxymethyl cellulose, gum arabic,poly(vinyl alcohol)s, turpentine, bran oil, bentonite, andligninsulfonates.

To improve the flowability of a solid product, the following adjuvantsmay also be used, namely, there may be used adjuvants such as waxes,stearates, alkyl phosphates, etc.

Adjuvants such as naphthalenesulfonic acid condensation products andpolycondensates of phosphates may be used as a peptizer for dispersibleproducts.

Adjuvants such as silicone oils may also be used as a defoaming agent.

Adjuvants such as 1,2-benzisothiazoline-3-one, parachlorometaxylenol,butyl paraoxybenzoate may also be added as a preservative.

Further, if necessary, functional spreading agents, active enhancerssuch as metabolic decomposition inhibitor like piperonyl butoxide,anti-freezing agents such as propylene glycol, antioxidants such as BHT,ultraviolet absorbers, and the like may also be added.

The content of the compound as active ingredient may be varied asrequired, and the compound as active ingredient may be used in aproportion properly chosen in the range of 0.01 to 90 parts by weightper 100 parts of the agrohorticultural insecticide. For example, industs or granules, the suitable content of the compound as activeingredient is from 0.01 to 50% by weight. In emulsifiable concentratesor wettable powders, it is also from 0.01 to 50% by weight.

The agrohorticultural insecticide of the present invention is used tocontrol a variety of insect pests in the following manner: it is appliedto a crop on which the insect pests are expected to appear, or a sitewhere appearance of the insect pests is undesirable, as it is or afterbeing properly diluted with or suspended in water or the like, in anamount effective for control of the insect pests.

The applying dosage of the agrohorticultural insecticide of the presentinvention is varied depending upon various factors such as a purpose,insect pests to be controlled, a growth state of a plant, tendency ofinsect pests appearance, weather, environmental conditions, apreparation form, an application method, an application site, andapplication time. It may be properly chosen in the range of 0.001 g to10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as activeingredient) per 10 are depending upon purposes.

The agrohorticultural insecticide of the present invention may be usedin admixture with other agrohorticultural insecticides, acaricides,nematocides, fungicides, biotic pesticides or the like in order toexpand both spectrum of controllable insect pest species and the periodof time when effective application are possible or to reduce the dosage.Furthermore, the agrohorticultural insecticide of the present inventionmay be used in admixture with herbicides, plant growth regulators,fertilizers or the like, depending upon application situations.

As the other agrohorticultural insecticides, acaricides, andnematocides, which are used for the above purpose, there can beexemplified agrohorticultural insecticides, acaricides, and nematocides,such as Ethion, Trichlorfon, Metamidophos, Acephate, Dichlorvos,Mevinphos, Monocrotophos, Malathion, Dimethoate, Formothion, Mecarbam,Vamidothion, Thiometon, Disulfoton, Oxydeprofos, Naled, Methylparathion,Fenitrothion, Cyanophos, Propaphosi Fenthion, Prothiofos, Profenofos,Isofenphos, Temephos, Phenthoate, Dimethylvinphos, Chlorfenvinphos,Tetrachlorvinphos, Phoxim, Isoxathion, Pyraclofos, Methidathion,Chlorpyrifos, Chlorpyrifos-methyl, Pyridaphenthion, Diazinon,Pirimiphosmethyl, Phosalone, Phosmet, Dioxabenzophos, Quinalphos,Terbuphos, Ethoprophos, Cadusafos, Mesulfenfos, DPS (NK-0795),Phosphocarb, Fenamiphos, Isoamidophos, Fosthiazate, Isazophos,Ethoprophos, Fenthion, Fostietane, Dichlofenthion, Thionazin, Sulprofos,Fensulfothion, Diamidafos, Pyrethrin, Allethrin, Prallethrin,Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropathrin,Cypermethrin, α-Cypermethrin, Cyhalothrin, λ-Cyhalothrin, Deltamethrin,Acrinathrin, Fenvalerate, Esfenvalerate, Flucythrinate, Fluvalinate,Cycloprothrin, Ethofenprox, Halfenprox, Silafluofen, Flucitrinate,Fluvalinate, Methomyl, Oxamyl, Thiodicarb, Aldicarb, Alanycarb, Cartap,Metolcarb, Xylylcarb, Propoxur, Phenoxycarb, Fenobucarb, Ethiophencarb,Fenothiocarb, Bifenazate, BPMC, Carbaryl, Pirimicarb, Carbofuran,Carbosulfan, Furathiocarb, Benfuracarb, Aldoxycarb, Diafenthiuron,Diflubenzuron, Teflubenzuron, Hexaflumuron, Novaluron, Lufenuron,Flufenoxuron, Chlorfluazuron, Fenbutatinoxide,tricyclohexyltinhydroxide, sodium oleate, potassium oleate, Methoprene,Hydroprene, Binapacryl, Amitraz, Dicofol, Kersen, Chrorobenzilate,Phenisobromolate, Tetradifon, Bensultap, Benzomate, Tebufenozide,Methoxyfenozide, Chromafenozide, Propargite, Acequinosyl, Endosulfan,Diofenolan, Chlorfenapyl, Fenpyroximate, Tolfenpyrad, Fipronil,Tebufenpyrad, Triazamate, Etoxazole, Hexythiazox, nicotine sulfate,Nitenpyram, Acetamiprid, Thiacloprid, Imidacloprid, Thiamethoxam,Clothianidin, Dinotefuran, Fluazinam, Pyriproxyfen, Hydramethylnon,Pyrimidifen, Pyridaben, Cyromazin, TPIC (tripropyl isocyanurate),Pymetrozin, Clofentezin, Buprofedin, Thiocyclam, Fenazaquin,Chinomethionate, Indoxacarb, Polynactin complexes, Milbemectin,Abamectin, Emamectin-benzoate, Spinosad, BT (Bacillus thuringiensis),Azadirachtin, Rotenone, hydroxypropyl starch, Levamisole hydrochloride,Metam-sodium, Morantel tartrate, Dazomet, Trichlamide, Pasteuria,Monacrosporium-phymatophagum, etc. As the agrohorticultural fungicidesused for the same purpose as above, there can be exemplifiedagrohorticultural fungicides such as sulfur, lime sulfur, copper sulfatebasic, Iprobenfos, Edifenfos, Tolclofos-methyl, Thiram, Polycarbamate,Zineb, Manzeb, Mancozeb, Propineb, Thiophanate, Thiophanate methyl,Benomyl, Iminoctadin acetate, Iminocutadin albecylate, Mepronil,Flutolanil, Pencycuron, Furametpyl, Thifluzamide, Metalaxyl, Oxadixyl,Carpropamid, Dichlofluanid, Flusulfamide, Chlorothalonil,Kresoxim-methyl, Fenoxanil (NNF-9425), Himexazol, Eclomezol,Fluoroimide, Procymidone, Vinclozolin, Iprodione, Triadimefon,Triflumizole, Bitertanol, Triflumizole, Ipconazole, Fluconazole,Propiconazole, Diphenoconazole, Myclobutanil, Tetraconazole,Hexaconazole, Tebuconazole, Imibenconazole, Prochloraz, Pefurazoate,Cyproconazole, Isoprothiolane, Fenarimol, Pyrimetanil, Mepanipyrim,Pyrifenox, Fluazinam, Triforine, Diclomezine, Azoxystrobin, Thiadiazin,Captan, Probenazole, Acibenzolar-S-methyl (CGA-245704), Fthalide,Tricyclazole, Pyroquilon, Chinomethionat, Oxolinic acid, Dithianon,Trifloxystrobin, Cyazofamid, Thiadinil, Dichlosimet, Kasugamycin,Validamycin, Polyoxin, Blasticidin, Streptomycin, etc. Similarly, as theherbicides, there can be exemplified herbicides such as Glyphosate,Sulfosate, Glyfosinate, Bialaphos, Butamifos, Esprocarb, Prosulcarb,Benthiocarb, Pyributycarb, Asulam, Linulon, Dymron, Bensulfuron-methyl,Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron ethyl, Azimsulfuron,Imazosulfuron, Tenylchlor, Alachlor, Pretilachlor, Clomeprop,Etobenzanid, Mefenacet, Pendimethalin, Bifenox, Acifluorfen, Lactfen,Cyhalofop-butyl, Ioxynil, Bromobutide, Alloxydim, Setoxydim,Napropamide, Indanofan, Pyrazolate, Benzofenap, Pyraflufen-ethyl,Imazapyl, Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat,Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn, Triazyflam,Benflesate, Flutiacet-methyl, Quizalofop-ethyl, Bentazon,Oxaziclomefone, Azafenidin, Benzobicyclone, calcium peroxide, etc.

As to the biotic pesticides, the same effect as above canbe expected byusing the agrohorticultural insecticide of the present invention inadmixture with, for example, viral formulations obtained from nuclearpolyhedrosis virus (NPV), granulosis virus (GV), cytoplasmicpolyhedrosis virus (CPV), entomopox virus (EPV), etc.; microbialpesticides utilized as insecticides or nematicides, such asMonacrosporium phymatophagum, Steinernema carpocapsae, Steinernemakushidai, Pasteuria penetrans, etc.; microbial pesticides utilized asfungicides, such as Trichoderma lignorum, Agrobacterium radiobactor,nonpathogenic Erwinia carotovora, Bacillus subtilis, etc.; and bioticpesticides utilized as herbicides, such as Xanthomonas campestris, etc.

In addition, the agrohorticultural insecticide of the present inventioncan be used in combination with biotic pesticides including naturalenemies such as Parasitic wasp (Encarsia formosa), Parasitic wasp(Aphidius colemani), Gall-mildge (Aphidoletes aphidimyza), Parasiticwasp (Diglyphus isaea), Parasitic mite (Dacnusa sibirica), Predatorymite (Phytoseiulus persimilis), Predatory mite (Amblyseius cucumeris),Predatory bug (Orius sauteri), etc.; microbial pesticides such asBeauveria brongniartii, etc.; and pheromones such as(Z)-10-tetradecenyl=acetate, (E,Z)-4,10-tetradecadienyl=acetate,(Z)-8-dodecenyl=acetate, (Z)-11-tetradecenyl=acetate,(Z)-13-icosen-10-one, (Z)-8-dodecenyl=acetate,(Z)-11-tetradecenyl=acetate, (Z)-13-icosen-10-one,14-methyl-1-octadecene, etc.

Typical formulation examples and test examples of the present inventionare described below but they should not be construed as limiting thescope of the invention.

As used in the formulation examples, the terms “part” and “parts” are byweight. Formulation Example 1 Each compound listed in Tables 1 to 3 10parts Xylene 70 parts N-methylprrolidone 10 parts Mixture ofpolyoxyethylene nonylphenyl ether 10 parts and calciumalkylbenzenesulfonate

An emulsifiable concentrate is prepared by mixing uniformly the aboveingredients to effect dissolution. Formulation Example 2 Each compoundlisted in Tables 1 to 3  3 parts Clay powder 82 parts Diatomaceous earthpowder 15 parts

A dust is prepared by mixing uniformly and grinding the aboveingredients. Formulation Example 3 Each compound listed in Tables 1 to 35 parts Mixed powder of bentonite and clay 90 parts Calciumligninsulfonate 5 parts

Granules are prepared by mixing the above ingredients uniformly, andkneading the resulting mixture together with a suitable amount of water,followed by granulation and drying. Formulation Example 4 Each compoundlisted in Tables 1 to 3 20 parts Kaolin and synthetic high- 75 partsdispersion silicic acid Mixture of polyoxyethylene nonylphenyl 5 partsether and calcium alkylbenzenesulfonate

A wettable powder is prepared by mixing uniformly and grinding the aboveingredients.

TEST EXAMPLE 1 Insecticidal Test on Diamond Back Moth (Plutellaxylostella)

Adult diamond back moths were released and allowed to ovipositonaChinese cabbage seedling. Twodays after the release, the seedlinghaving the eggs deposited thereon was immersed for about 30 seconds in aliquid chemical prepared by diluting a preparation containing eachcompound listed in Tables 1 to 3 as an active ingredient to adjust theconcentration to 50 ppm. After air-dryness, it was allowed to stand in aroom thermostatted at 25° C. Six days after the immersion, the hatchedinsects were counted. The mortality was calculated according to thefollowing equation and the insecticidal effect was judged according tothe criterion shown below. The test was carried out with triplicategroups of 10 insects.${{Corrected}\quad{mortality}\quad(\%)} = {\frac{\begin{matrix}{{Number}\quad{of}} \\{{hatched}\quad{insects}} \\{{in}\quad{untreated}\quad{group}}\end{matrix} - \begin{matrix}{{Number}\quad{of}} \\{{hatched}\quad{insects}} \\{{in}\quad{treated}\quad{group}}\end{matrix}}{\begin{matrix}{{Number}\quad{of}\quad{hatched}\quad{insects}} \\{{in}\quad{untreated}\quad{group}}\end{matrix}} \times 100}$ Criterion: A --- Mortality 100% B ---Mortality 99-90% C --- Mortality 89-80% D --- Mortality 79-50% E ---Mortality 49% or less

The result is shown in Table 4 below.

TEST EXAMPLE 2 Insecticidal Test on Common Cutworm (Spodoptera litura)

A piece of cabbage leaf (cultivar; Shikidori) was immersed for about 30seconds in a liquid chemical prepared by diluting a preparationcontaining each compound listed in Tables 1 to 3 as an active ingredientto adjust the concentration to 50 ppm. After air-dryness, it was placedin a plastic Petri dish with a diameter of 9 cm and inoculated withsecond-instar larvae of common cutworm, after which the dish was closedand then allowed to stand in a room thermostatted at 25° C. Eight daysafter the inoculation, the dead and alive were counted. The mortalitywas calculated according to the following equation and the insecticidaleffect was judged according to the criterion shown in Test Example 1.The test was carried out with triplicate groups of 10 insects.${{Corrected}\quad{mortality}\quad(\%)} = {\frac{\begin{matrix}{{Number}\quad{of}} \\{{alive}\quad{larvae}\quad{in}} \\{{untreated}\quad{group}}\end{matrix} - \begin{matrix}{{Number}\quad{of}} \\{{alive}\quad{larvae}\quad{in}} \\{{treated}\quad{group}}\end{matrix}}{\begin{matrix}{{Number}\quad{of}\quad{alive}\quad{larvae}} \\{{in}\quad{treated}\quad{group}}\end{matrix}} \times 100}$

The result is shown in Table 4 below.

TEST EXAMPLE 3 Insecticidal Test on Smaller Tea Tortrix (Adoxophyes Sp.)

Tea leaves were immersed for about 30 seconds in a liquid chemicalprepared by diluting a preparation containing each compound listed inTables 1 to 3 as an active ingredient to adjust the concentration to 50ppm. After air-dryness, the tea leaves were placed in a plastic Petridish with a diameter of 9 cm and inoculated with larvae of smaller teatortrix, after which the dish was allowed to stand in a roomthermostatted at 25° C. and having a humidity of 70%. Eight days afterthe inoculation, the dead and alive larvae were counted and, themortality was calculated according to the equation shown in Test Example2, and the insecticidal effect was judged according to the criterionshown in Test Example 1. The test was carried out with triplicate groupsof 10 insects.

The result is shown in Table 4 below. TABLE 4 Test Test Test No. Example1 Example 2 Example 3 1-290 A A A 1-292 A A A 1-296 A A A 1-297 A A A1-298 A A A 1-372 A A A 1-374 A A A 1-458 A A A 1-459 A A A 1-460 A A A2-22 A A A 2-23 A A E 2-24 A A A 3-5 A E A 3-6 A D E 3-7 A A A 3-24 A AA 3-26 A A A

1-4. (canceled)
 5. A phthalamide derivative of formula (I):

wherein R¹ represents hydrogen; C₃₋₆ cycloalkyl; halo C₃₋₆ cycloalkyl;phenyl; substituted phenyl having one or more substituents, which may bethe same or different, selected from the group consisting of halogen,C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl;heterocyclyl; substituted heterocyclyl having one or more substituents,which may be the same or different, selected from the group consistingof halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; or thegroup -A-(G)r, R² and R³, which may be the same or different, representhydrogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₃₋₆ alkenyl, halo C₃₋₆ alkenyl,C₃₋₆ alkynyl, halo C₃₋₆ alkynyl, C₃₋₆ cycloalkyl, halo C₃₋₆ cycloalkyl,C₁₋₆ alkoxy C₁₋₆ alkyl, C₁₋₆ alkylthio C₁₋₆ alkyl, formyl, C₁₋₆alkylcarbonyl, halo C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, mono C₁₋₆alkylaminocarbonyl, or same or different di C₁₋₆ alkylaminocarbonyl; orR² together with A, R¹, G, R⁴, or R⁶ optionally forms a 4- to 8-memberedring that is optionally interrupted with 1 or 2 oxygen, sulfur, ornitrogen, which may be the same or different; each X, which may be thesame or different, represents halogen, nitro, amino, mono C₁₋₆alkylamino, same or different di C₁₋₆ alkylamino, C₁₋₆alkylcarbonylamino, halo C₁₋₆ alkylcarbonylamino, C₁₋₆alkylsulfonylamino, halo C₁₋₆ alkylsulfonylamino, cyano, C₁₋₆ alkyl,halo C₁₋₆ alkyl, C₂₋₆ alkenyl, halo C₂₋₆ alkenyl, C₂₋₆ alkynyl, haloC₂₋₆ alkynyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylcarbonyloxy, haloC₁₋₆ alkylcarbonyloxy, C₁₋₆ alkylsulfonyloxy, halo C₁₋₆alkylsulfonyloxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; or two groups X that are adjacent to each other on anaromatic ring optionally together form a fused ring, which optionallyhas one or more substituents, which may be the same or different,selected from the group consisting of halogen, cyano, nitro, C₁₋₆ alkyl,halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, haloC₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; m represents an integer of 0to 2; each Y, which may be the same or different, represents halogen;nitro; cyano; C₁₋₆ alkyl; halo C₁₋₆ alkyl; cyclo C₃₋₆ alkyl; C₁₋₆alkoxy; halo C₁₋₆ alkoxy; mono C₁₋₆ alkylamino; same or different diC₁₋₆ alkylamino; C₁₋₆ alkylthio; halo C₁₋₆ alkylthio; C₁₋₆alkylsulfinyl; halo C₁₋₆ alkylsulfinyl; C₁₋₆ alkylsulfonyl; halo C₁₋₆alkylsulfonyl; phenyl; substituted phenyl having one or moresubstituents, which may be the same or different, selected from thegroup consisting of halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy,halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, and haloC₁₋₆ alkylsulfonyl; phenyl C₁₋₄ alkyl; substituted phenyl C₁₋₄ alkylhaving on a ring one or more substituents, which may be the same ordifferent, selected from the group consisting of halogen, C₁₋₆ alkyl,halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, haloC₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; phenoxy; substituted phenoxyhaving one or more substituents, which may be the same or different,selected from the group consisting of halogen, C₁₋₆ alkyl, halo C₁₋₆alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; phenylthio; substitutedphenylthio having one or more substituents, which may be the same ordifferent, selected from the group consisting of halogen, C₁₋₆ alkyl,halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, haloC₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; heterocyclyl; or substitutedheterocyclyl having one or more substituents, which may be the same ordifferent, selected from the group consisting of halogen, cyano, nitro,C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; and twogroups Y adjacent to each other on an aromatic ring may together form afused ring, which optionally has one or more substituents, which may bethe same or different, and selected from the group consisting ofhalogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; or Ytogether with R³ optionally forms a 5- to 7-membered ring that may beinterrupted with 1 or 2 oxygen, sulfur, or nitrogen, which may be thesame or different; n represents an integer of 0 to 3, A represents C₁₋₈alkylene, C₃₋₆ alkenylene, or C₃₋₆ alkynylene; each G, which may be thesame or different, represents hydrogen; halogen; cyano; nitro; halo C₁₋₆alkyl; C₃₋₆ cycloalkyl; halo C₃₋₆ cycloalkyl; same or different di C₁₋₆alkoxyphosphoryl; same or different di C₁₋₆ alkoxythiophosphoryl;diphenylphosphino; diphenylphosphono; same or different C₁₋₆dialkylsulfonium; phenyl; substituted phenyl having one or moresubstituents, which may be the same or different, selected from thegroup consisting of halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy,halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, and haloC₁₋₆ alkylsulfonyl; heterocyclyl; substituted heterocyclyl having one ormore substituents, which may be the same or different, selected from thegroup consisting of halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy,halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, and haloC₁₋₆ alkylsulfonyl; or the group —Z—R⁴, r represents an integer of 1 to3, z represents —O— or —N(R⁵)— R⁵ represents hydrogen; C₁₋₆alkylcarbonyl; halo C₁₋₆ alkylcarbonyl; C₁₋₆ alkoxycarbonyl;phenylcarbonyl; substituted phenylcarbonyl having one or moresubstituents, which may be the same or different, selected from thegroup consisting of halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy,halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; C₁₋₆ alkylsulfonyl; and halo C₁₋₆ alkylsulfonyl; R⁴represents hydrogen; C₁₋₆ alkyl; halo C₁₋₆ alkyl; C₃₋₆ alkenyl; haloC₃₋₆ alkenyl; C₃₋₆ alkynyl; halo C₃₋₆ alkynyl; C₃₋₆ cycloalkyl; haloC₃₋₆ cycloalkyl; C₁₋₆ C₁₋₆ alkyl; C₁₋₆ alkylthio C₁₋₆ alkyl; formyl;C₁₋₆ alkylcarbonyl; halo C₁₋₆ alkylcarbonyl; C₁₋₆ alkoxycarbonyl; monoC₁₋₆ alkylaminocarbonyl; same or different di C₁₋₆ alkylaminocarbonyl;mono C₁₋₆ alkylaminothiocarbonyl; same or different di C₁₋₆alkylaminothiocarbonyl; same or different di C₁₋₆ alkoxyphosphoryl; sameor different di C₁₋₆ alkoxythiophosphoryl; phenyl; substituted phenylhaving one or more substituents, which may be the same or different, andselected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, haloC₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl,halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;phenyl C₁₋₄ alkyl; substituted phenyl C₁₋₄ alkyl having on a ring one ormore substituents, which may be the same or different, and selected fromhalogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl;heterocyclyl; or substituted heterocyclyl having one or moresubstituents, which may be the same or different, and selected fromhalogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, and halo C₁₋₆ alkylsulfonyl; or thegroup —W—R⁶, w represents —S—, —SO—, —SO₂—, —C(═O)—, —C(═S)—, or thegroup —C(═NOR⁷)— R⁷ represents hydrogen; C₁₋₆ alkyl; halo C₁₋₆ alkyl;C₃₋₆ alkenyl; halo C₃₋₆ alkenyl; C₃₋₆ alkynyl; C₃₋₆ cycloalkyl; phenylC₁₋₄ alkyl; or substituted phenyl C₁₋₄ alkyl having on a ring one ormore substituents, which may be the same or different, and selected fromhalogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy,C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl, and R⁶represents hydrogen; C₁₋₆ alkyl; halo C₁₋₆ alkyl; C₃₋₆ alkenyl; haloC₃₋₆ alkenyl; C₃₋₆ alkynyl; halo C₃₋₆ alkynyl; C₃₋₆ cycloalkyl; haloC₃₋₆ cycloalkyl; C₁₋₆ alkox C₁₋₆ alkyl; C₁₋₆ alkylthio C₁₋₆ alkyl; C₁₋₆alkoxy; halo C₁₋₆ alkoxy; C₁₋₆ alkylthio; halo C₁₋₆ alkylthio; amino;mono C₁₋₆ alkylamino; same or different di C₁₋₆ alkylamino; C₁₋₆ alkoxyC₁₋₆ alkylamino; C₁₋₆ alkylthio C₁₋₆ alkylamino; phenyl; substitutedphenyl having one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; phenyl C₁₋₄ alkyl; substituted phenyl C₁₋₄ alkyl havingon a ring one or more substituents, which may be the same or different,and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆ alkoxy,halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; phenylamino; substituted phenylamino having on a ring oneor more substituents, which may be the same or different, selected fromthe group consisting of halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; phenyl C₁₋₄ alkylamino; substituted phenyl C₁₋₄alkylamino having on a ring one or more substituents, which may be thesame or different, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆alkyl, C₁₋₆ alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆alkylthio, C₁₋₆ alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆alkylsulfonyl, or halo C₁₋₆ alkylsulfonyl; heterocyclyl; substitutedheterocyclyl having one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; heterocyclic amino; or substituted heterocyclic aminohaving on a ring one or more substituents, which may be the same ordifferent, and selected from halogen, C₁₋₆ alkyl, halo C₁₋₆ alkyl, C₁₋₆alkoxy, halo C₁₋₆ alkoxy, C₁₋₆ alkylthio, halo C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, halo C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or halo C₁₋₆alkylsulfonyl; or R⁴ or R⁶ together with A optionally form a 4- to8-membered ring that may be interrupted with 1 or 2 oxygen, sulfur, ornitrogen, which may be the same or different.
 6. A phthalamidederivative according to claim 5 wherein R¹ represents C₁₋₆ alkyl, C₁₋₆alkylthio C₁₋₆ alkyl, C₁₋₆ alkylsulfinyl C₁₋₆ alkyl, or C₁₋₆alkylsulfonyl C₁₋₆ alkyl; R² and R³ represent hydrogen; x representshalogen; m represents 1; Y represents halogen or C₁₋₆ alkyl; and nrepresents an integer of 0 to
 2. 7. An agrohorticultural insecticidecomprising one or more phthalamide derivatives according to claim 5 asan active ingredient and one or more inert carriers and optionally oneor more adjuvants.
 8. A method for using an agrohorticulturalinsecticide to protect a useful plant from insect pests comprisingapplying an effective amount of a agrohorticultural insecticideaccording to claim 7 to a crop plant or to the soil.